Potassium Carbonate → Methyl 3-[1-(3-isobutylphenyl)ethyl]benzoate

HRID 249150Notes

Reaction equation

O[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH:16]=1)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:21]([C:17]1[CH:16]=[C:15]([CH:13]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH3:14])[CH:20]=[CH:19][CH:18]=1)[CH:22]([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of methyl 3-hydroxybenzoate (939 mg), 1-(1-bromoethyl)-3-isobutylbenzene (1.49 g) and potassium carbonate (1.71 g) in N,N-dimethylformamide (20 ml) was stirred at 25° C. overnight. The mixture was partitioned between ether and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (30 g) eluting with a mixture of ethyl acetate and hexane (1:10) to give methyl 3-[1-(3-isobutylphenyl)ethyl]benzoate (1.45 g) as an oil.

Workup

customThe mixture was partitioned between ether and 1N hydrochloric acid
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was chromatographed on silica gel (30 g)
washeluting with a mixture of ethyl acetate and hexane (1:10)

Sources & evidence

ORD record: ord-6f3ac6ae116945d0b3416216a399fa73
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05212320

Reaction notes

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