Tert butyl carboxylic acid

Tert butyl carboxylic acid DEFAULT

tert-Butyl esters

Organic Chemistry Portal

Reactions >> Protecting Groups >> Stability

T. W. Green, P. G. M. Wuts,
Protective Groups in Organic Synthesis,
Wiley-Interscience, New York, , , ,

Stability

H2O:pH < 1, °CpH = 1, RTpH = 4, RTpH = 9, RTpH = 12, RTpH > 12, °C
Bases:LDANEt3, Pyt-BuOKOthers:DCCSOCl2
Nucleophiles:RLiRMgXRCuLiEnolatesNH3, RNH2NaOCH3
Electrophiles:RCOClRCHOCH3IOthers::CCl2Bu3SnH
Reduction:H2 / NiH2 / RhZn / HClNa / NH3LiAlH4NaBH4
Oxidation:KMnO4OsO4CrO3 / PyRCOOOHI2, Br2, Cl2MnO2 / CH2Cl2

Deprotection


Aqueous phosphoric acid is an effective, environmentally benign, selective and mild reagent for the deprotection of tert-butyl carbamates, tert-butyl esters, and tert-butyl ethers. CBZ carbamates, azetidine, benzyl and methyl esters, TBDMS, and methyl phenyl ethers are tolerated. The reactions are high yielding, and the workup is convenient.
B. Li, M. Berliner, R. Buzon, C. K.-F. Chiu, S. T. Colgan, T. Kaneko, N. Keene, W. Kissel, T. Le, K. R. Leeman, B. Marquez, R. Morris, L. Newell, S. Wunderwald, M. Witt, J. Weaver, Z. Zhang, Z. Zhang, J. Org. Chem., , 71,


The hazardous Schmidt procedure for tert-butyl benzoate ester cleavage using NaH in DMF involves BAC2 ester cleavage by NaH-derived NaOH, rather than the proposed E2 elimination of isobutylene by DMF-derived NaNMe2. Powdered KOH in THF is a significantly safer and simpler alternative that effects cleavage of tert-butyl benozoates at ambient temperature in excellent yield.
E. Filali, G. C. Lloyd-Jones, D. A. Sale, Synlett, ,


E. Filali, G. C. Lloyd-Jones, D. A. Sale, Synlett, ,


An interesting example of a selective deprotection of tert-butyl esters is reported.
E. Marcantoni, M. Massaccesi, E. Torregiani, G. Bartoli, M. Bosco, L. Sambri, J. Org. Chem, , 66,


Conversion of tert-butyl esters to other functional groups


The reaction of tert-butyl esters with SOCl2 at room temperature provides acid chlorides in very good yields, whereas benzyl, methyl, ethyl, and isopropyl esters are essentially unreactive.
J. A. Greenberg, T. Sammakia, J. Org. Chem., , 82,

Sours: https://www.organic-chemistry.org/protectivegroups/carboxyl/tert-butyl-esters.htm

3-(tert-Butyl)methyl-1H-pyrazole-carboxylic acid, 95%, Thermo Scientific™

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  • 3-(tert-Butyl)methyl-1H-pyrazole-carboxylic acid, 95%, Thermo Scientific&trade;: Carboxylic acids and derivatives Organic acids and derivatives
  • 3-(tert-Butyl)methyl-1H-pyrazole-carboxylic acid, 95%, Thermo Scientific&trade;: Carboxylic acids and derivatives Organic acids and derivatives

Chemical Identifiers

CAS
Molecular FormulaC9H14N2O2
Molecular Weight (g/mol)
InChI KeySFSXXMXHJOSBAZ-UHFFFAOYSA-N
Synonym3-tert-butylmethyl-1h-pyrazolecarboxylic acid, 3-tert-butylmethylpyrazolecarboxylic acid, 5-tert-butylmethyl-2h-pyrazolecarboxylic acid, 1h-pyrazolecarboxylic acid, ,1-dimethylethylmethyl, 3-t-butylmethyl-1h-pyrazolecarboxylic acid, maybridge1_, acmc-1bzn5, butylmethylpyrazolecarboxylicacid
PubChem CID
IUPAC Name5-tert-butylmethylpyrazolecarboxylic acid
SMILESCC(C)(C)C1=NN(C(=C1)C(=O)O)C
View More Specs

Products 2DescriptionSpecifications

Chemical Identifiers

3-tert-butylmethyl-1h-pyrazolecarboxylic acid, 3-tert-butylmethylpyrazolecarboxylic acid, 5-tert-butylmethyl-2h-pyrazolecarboxylic acid, 1h-pyrazolecarboxylic acid, ,1-dimethylethylmethyl, 3-t-butylmethyl-1h-pyrazolecarboxylic acid, maybridge1_, acmc-1bzn5, butylmethylpyrazolecarboxylicacid
5-tert-butylmethylpyrazolecarboxylic acid
C9H14N2O2
SFSXXMXHJOSBAZ-UHFFFAOYSA-N
CC(C)(C)C1=NN(C(=C1)C(=O)O)C

Specifications

3-(tert-Butyl)methyl-1H-pyrazole-carboxylic acid
°C to °C
C9H14N2O2
SFSXXMXHJOSBAZ-UHFFFAOYSA-N
5-tert-butylmethylpyrazolecarboxylic acid
95%
Authentic
5g
96% min. (HPLC)
3-tert-butylmethyl-1h-pyrazolecarboxylic acid, 3-tert-butylmethylpyrazolecarboxylic acid, 5-tert-butylmethyl-2h-pyrazolecarboxylic acid, 1h-pyrazolecarboxylic acid, ,1-dimethylethylmethyl, 3-t-butylmethyl-1h-pyrazolecarboxylic acid, maybridge1_, acmc-1bzn5, butylmethylpyrazolecarboxylicacid
CC(C)(C)C1=NN(C(=C1)C(=O)O)C
Safety and Handling

Safety and Handling

Product Identifier
  • 3-(tert-Butyl)methyl-1H-pyrazole-carboxylic acid, 95%

Signal Word
Hazard Category
  • Serious eye damage/eye irritation Category 2
  • Skin corrosion/irritation Category 2
  • Specific target organ toxicity Category 3

Hazard Statement
  • HCauses serious eye irritation.
  • HMay cause respiratory irritation.
  • HCauses skin irritation.

Precautionary Statement
  • PAvoid breathing dust/fume/gas/mist/vapours/spray.
  • PWear protective gloves/protective clothing/eye protection/face protection.
  • P+PIF ON SKIN: Wash with plenty of water/.
  • P+P+PIF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

SDS Product Certifications
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Pivalic acid

Chemical compound

Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (t-BuC(O)) is Piv and for pivalic acid (t-BuC(O)OH) is PivOH.

Preparation[edit]

Industrial route[edit]

Pivalic acid is prepared by hydrocarboxylation of isobutene via the Koch reaction:

(CH3)2C=CH2 + CO + H2O → (CH3)3CCO2H

Such reactions require an acid catalyst such as hydrogen fluoride. tert-Butyl alcohol and isobutyl alcohol can also be used in place of isobutene. Globally, several million kilograms are produced annually.[1] Pivalic acid is also economically recovered as a by-product from the production of semi-synthetic penicillins like ampicillin and amoxycillin.

Laboratory methods[edit]

It was originally prepared by the oxidation of pinacolone with chromic acid[2] and by the hydrolysis of tert-butyl cyanide.[3] Convenient laboratory routes proceed via tert-butyl chloride via carbonation of the Grignard reagent[4] and by oxidation of pinacolone.[5]

t-Butylmagnesium bromide reacts with CO2to form the pivalate salt. Addition of acid yields pivalic acid

Applications[edit]

Relative to esters of most carboxylic acids, esters of pivalic acid are unusually resistant to hydrolysis. Some applications result from this thermal stability. Polymers derived from pivalate esters of vinyl alcohol are highly reflective lacquers. The pivaloyl (abbreviated Piv or Pv) group is a protective group for alcohols in organic synthesis. Pivalic acid is sometimes used as an internal chemical shift standard for NMR spectra of aqueous solutions. While DSS is more commonly used for this purpose, the minor peaks from protons on the three methylene bridges in DSS can be problematic. The 1H NMR spectrum at 25&#;°C and neutral pH is a singlet at ppm. Pivalic acid is employed as co-catalyst in some of the Palladium catalyzed C-H functionalization reaction.[6][7]

Alcohol protection[edit]

The pivaloyl group is used as a protecting group in organic synthesis. Common protection methods include treatment of alcohol with pivaloyl chloride (PvCl) in presence of pyridine.[8]

PvProtectedAlcohol.png

Alternatively, the esters can be prepared using pivaloic anhydride in the presence of scandium triflate (Sc(OTf)3) or vanadyl triflate (VO(OTf)2).

Common deprotection methods involve hydrolysis with a base or other nucleophiles.[9][10][11][12]

PvProtection.png

See also[edit]

References[edit]

  1. ^Riemenschneider, Wilhelm (). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi/a05_ ISBN&#;.
  2. ^Friedel and Silva, Ber. 6, , ().[full citation needed]
  3. ^Butlerow, Ann. , ().[full citation needed]
  4. ^S. V. Puntambeker; E. A. Zoellner; L. T. Sandborn; E. W. Bousquet (). "Trimethylacetic acid from tert.- Butyl Chloride". Organic Syntheses. doi/orgsyn; Collective Volume, 1, p.&#;
  5. ^L. T. Sandborn; E. W. Bousquet (). "Trimethylacetic acid from Pinacolone". Organic Syntheses. doi/orgsyn; Collective Volume, 1, p.&#;
  6. ^Lafrance, Marc; Fagnou, Keith (). "Palladium-catalyzed benzene arylation: incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design". Journal of the American Chemical Society. (51): – doi/jaj. ISSN&#; PMID&#;
  7. ^Zhao, Dongbing; Wang, Weida; Lian, Shuang; Yang, Fei; Lan, Jingbo; You, Jingsong (). "Phosphine-Free, Palladium-Catalyzed Arylation of Heterocycles through CH Bond Activation with Pivalic Acid as a Cocatalyst". Chemistry – A European Journal. 15 (6): – doi/chem ISSN&#;
  8. ^Robins, Morris J.; Hawrelak, S. D.; Kanai, Tadashi; Siefert, Jan Marcus; Mengel, Rudolf (). "Nucleic acid related compounds. Transformations of adenosine to the first 2',3'-aziridine-fused nucleosides, 9-(2,3-epimino-2,3-dideoxy-.beta.-D-ribofuranosyl)adenine and 9-(2,3-epimino-2,3-dideoxy-.beta.-D-lyxofuranosyl)adenine". The Journal of Organic Chemistry. 44 (8): – doi/joa
  9. ^Van Boeckel, C.A.A.; Van Boom, J.H. (). "Synthesis of glucosylphosphatidylglycerol via a phosphotriester intermediate". Tetrahedron Letters. 20 (37): –4. doi/S(01)
  10. ^Griffin, B.E.; Jarman, M.; Reese, C.B. (). "The Synthesis of oligoribonucleotides—IV". Tetrahedron. 24 (2): – doi/(68) PMID&#;
  11. ^Ogilvie, Kelvin K.; Iwacha, Donald J. (). "Use of the tert-butyldimethylsilyl group for protecting the hydroxyl functions of nucleosides". Tetrahedron Letters. 14 (4): –9. doi/S(01)
  12. ^Paquette, Leo A.; Collado, Iván; Purdie, Mark (). "Total Synthesis of Spinosyn A. 2. Degradation Studies Involving the Pure Factor and Its Complete Reconstitution". Journal of the American Chemical Society. (11): – doi/jak. INIST
Sours: https://en.wikipedia.org/wiki/Pivalic_acid

Cyclobutane carboxylic acid, 3-tert-butyl, ethyl ester, cis-


Reaction thermochemistry data

Go To:Top, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by:Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Ethyl transt-butylcyclobutanecarboxylate = Cyclobutane carboxylic acid, 3-tert-butyl, ethyl ester, cis-

By formula: C11H20O2 = C11H20O2


References

Go To:Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Lampman, Hager, et al.,
Lampman, G.M.; Hager, G.D.; Couchman, G.L., Enthalpy, entropy, and free-energy changes in the equilibrium of cis- and trans-ethyl 3-t-butylcyclobutanecarboxylate and 3-t-butylcyclobutanol, J. Org. Chem., , 35, [all data]


Notes

Go To:Top, Reaction thermochemistry data, References

  • Symbols used in this document:
    &#;rEnthalpy of reaction at standard conditions
  • Data from NIST Standard Reference Database NIST Chemistry WebBook
  • The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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Butyl acid tert carboxylic

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Naming of Acid Derivatives

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