Phenol → Tert-butyl 3-methyl-4-phenoxybenzoate

HRID 1501034Notes

Reaction equation

F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH3:15].[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:15][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:2]=1[O:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl 4-fluoro-3-methylbenzoate (740 mg, 3.5 mmol), phenol (700 mg, 7.4 mmol), potassium carbonate (993 mg, 7.2 mmol) and methylsulfinylmethane (10 mL) was stirred at 120° C. for 12 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=80:1) to give tert-butyl 3-methyl-4-phenoxybenzoate as a colorless oil (654 mg, 66%). 1H NMR (300 MHz, CDCl3): δ 8.08 (s, 1H), 7.68 (s, 1H), 7.38 (s, 1H), 7.32-7.28 (m, 2H), 6.84-6.77 (m, 3H), 2.26 (s, 3H), 1.56 (s, 9H).

Workup

concentrationThe mixture was concentrated
customto give a residue
customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=80:1)

Sources & evidence

ORD record: ord-386a4b1d23224d3e9547db33efe3d07f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206128B2

Reaction notes

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