1-Propanol → Benzeneacetic acid, propyl ester

HRID 1411165Notes

Reaction equation

HRID 1411165 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:23])[CH2:21][CH3:22]>>[C:1]1([CH2:7][C:8]([O:23][CH2:20][CH2:21][CH3:22])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 10311-PropanolHCID 1140TolueneHCID 8033Di-tert-butyl peroxideHCID 178418416HCID 178418416, compound2×

Product 1

HCID 221641Benzeneacetic acid, propyl esterYield 88%

Conditions

Temperature
120 °C

Procedure

Toluene (1.38 g), n-propanol (60 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 78 mg n-propyl phenylacetate was obtained by column chromatography, in a yield of 88%. 1HNMR (400 MHz, CDCl3) δ 0.88 (t, J=7.6 Hz, 3H), 1.59-1.67 (m, 2H), 3.61 (s, 2H), 4.12 (t, J=6.8 Hz, 2H), 7.23-7.33 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 10.3, 21.9, 41.5, 66.4, 127.0, 129.3, 134.3, 171.7; HRMS (ESI) calcd. for C11H14NaO2 [M+Na]: 201.0886. found: 201.0886. The n-propyl 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, 56 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94%.

Workup

  1. additionwas introduced

Sources & evidence

ORD record
ord-7f48d7b0f8774bd7a2fc2151f6cce186
Source dataset
uspto-grants-2014_12
Patent number
US08921591B2

Reaction notes

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