Toluene → Isobutyl phenylacetate

HRID 1411167Notes

Reaction equation

HRID 1411167 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O:12]OC(C)(C)C)(C)(C)C.[C]=O.[CH2:20]([OH:24])[CH:21]([CH3:23])[CH3:22]>>[C:1]1([CH2:7][C:8]([O:24][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 6560IsobutanolHCID 8033Di-tert-butyl peroxideHCID 178418416HCID 178418416, compound2×

Product 1

HCID 60998Isobutyl phenylacetateYield 72%

Conditions

Temperature
120 °C

Procedure

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%.

Workup

  1. additionwas introduced

Sources & evidence

ORD record
ord-94af7497fa824cca9e081ed54f314041
Source dataset
uspto-grants-2014_12
Patent number
US08921591B2

Reaction notes

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