1-Butanol → Benzeneacetic acid, butyl ester

HRID 1411166Notes

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])[CH2:21][CH2:22][CH3:23]>>[C:1]1([CH2:7][C:8]([O:24][CH2:20][CH2:21][CH2:22][CH3:23])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 4

HCID 2631-Butanol

HCID 1140Toluene

HCID 8033Di-tert-butyl peroxide

HCID 178418416HCID 178418416, compound2×

Product 1

HCID 31210Benzeneacetic acid, butyl esterYield 68%

Conditions

Temperature: 120 °C

Procedure

Toluene (1.38 g), n-butanol (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 65 mg n-butyl phenylacetate was obtained by column chromatography, in a yield of 68%. 1HNMR (400 MHz, CDCl3) δ 0.88 (t, J=7.6 Hz, 3H), 1.29-1.38 (m, 2H), 1.55-1.62 (m, 2H), 3.60 (s, 2H), 4.06 (t, J=6.8 Hz, 2H), 7.23-7.33 (m, 5H); 13CNMR (100 MHz, CDCl3) δ 13.7, 19.1, 30.6, 41.5, 64.7, 127.0, 128.5, 129.3, 134.3, 171.7; HRMS (ESI) calcd. for C12H16NaO2 [M+Na]: 215.1043. found: 215.1042. The n-butyl 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, 43 mg product phenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94%.

Workup

additionwas introduced

Sources & evidence

ORD record: ord-eea0b11033884ff082c7895b70bed22b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921591B2

Reaction notes

Loading…