ChemicalBook CAS DataBase List Phenylacetic acid isobutyl ester

Phenylacetic acid isobutyl ester synthesis

9synthesis methods

Product Name:Phenylacetic acid isobutyl ester
CAS Number:102-13-6
Molecular formula:C12H16O2
Molecular Weight:192.25

By esterification of phenylacetic acid with isobutyl alcohol.

78-83-1 Synthesis

78-83-1
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201230-82-2 Synthesis

201230-82-2
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108-88-3
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$21.80/5 mL

102-13-6
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$26.00/25mL

Yield:102-13-6 72%

Reaction Conditions:

with di-tert-butyl peroxide;dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II) at 120; under 7600.51 Torr; for 16 h;

Steps:

6 Preparation of Phenylacetic Acid from Toluene and Isobutanol
Toluene (1.38 g), isobutanol (74 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl₂(3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 69 mg isobutyl phenylacetate was obtained by column chromatography, in a yield of 72%. ¹HNMR (400 MHz, CDCl₃) δ 0.88 (s, 3H), 0.89 (s, 3H), 1.85-1.96 (m, 1H), 3.62 (s, 2H), 3.86 (d, J=6.8 Hz, 1H), 7.23-7.34 (m, 5H); ¹³CNMR (100 MHz, CDCl₃) δ 19.0, 27.7, 41.5, 70.9, 127.0, 128.5, 129.3, 134.3, 171.6; HRMS (ESI) calcd. for C₁₂H₁₆NaO₂[M+Na]: 215.1043. found: 215.1037. The isobutyl phenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 53 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 93%.

References:

Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences;Huang, Hanmin;Xia, Chungu;Xie, Pan US2013/303798, 2013, A1 Location in patent:Paragraph 0038; 0039

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