Ethanol → Ethyl 3,5-dimethylphenylacetate

HRID 1411176Notes

Reaction equation

[C:1]1([CH3:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.C(O[O:15][C:16]([CH3:19])(C)C)(C)(C)C.[C]=O.[CH2:22]([OH:24])C>>[CH3:9][C:1]1[CH:6]=[C:5]([CH2:7][C:22]([O:15][CH2:16][CH3:19])=[O:24])[CH:4]=[C:3]([CH3:8])[CH:2]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 7947Mesitylene

HCID 8033Di-tert-butyl peroxide

HCID 178418416HCID 178418416, compound2×

Product 1

HCID 7021465Ethyl 3,5-dimethylphenylacetateYield 89%

Conditions

Temperature: 120 °C

Procedure

Mesitylene (1.8 g), ethanol (46 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 85 mg ethyl 3,5-dimethylphenylacetate was obtained by column chromatography, in a yield of 89%. 1HNMR (400 MHz, CDCl3) δ 1.24 (t, J=7.2 Hz, 3H), 2.30 (s, 6H), 3.53 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 6.84-6.95 (m, 3H); 13CNMR (100 MHz, CDCl3) δ 14.2, 21.3, 41.3, 60.8, 127.0, 128.7, 133.9, 138.1, 171.9; HRMS (ESI) calcd. for C12H16NaO2 [M+Na]: 215.1043. found: 215.1040. The ethyl 3,5-dimethylphenylacetate 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, 70 mg product 3,5-dimethylphenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 96%.

Workup

additionwas introduced

Sources & evidence

ORD record: ord-3a1aa837ec464ad68c9b2400ac6c97a2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921591B2

Reaction notes

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