Water → Methyl {4-[(4-hydroxyphenyl)carbonyl]phenyl}acetate

HRID 2100133Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)=[O:12])=[CH:7][CH:6]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)=[O:12])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of methyl(4-{[4-(methyloxy)phenyl]carbonyl}phenyl)acetate (151) (1.00 g, 3.52 mmol) and AlCl3 (1.90 g, 14.07 mmol) were refluxed in benzene (40 mL) for 1 h and then cooled to 0° C. in an ice bath. Water (35 mL) was added slowly, and the mixture was extracted with ether (2×50 mL, each contained 15 mL of EtOAc). The combined ethereal extract washed with water, brine, and dried over Na2SO4. Concentration gave light brown oil, which was purified by chromatography on a silica gel column eluted with a gradient from hexanes to 45% EtOAc:hexanes to afford 0.86 g (90%) of compound 152 as colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71 (s, 2H), 3.72 (s, 3H), 5.63 (br s, 1H), 6.89 (d, J=8.6 Hz, 2H), 7.38 (d, J=8.0 Hz, 2H), 7.72 (d, J=8.1 Hz, 2H), 7.77 (d, J=8.6 Hz, 2H), 8.24 (d, J=7.9 Hz, 1H). LCMS (ESI): m/z 271 (M+H)+, 269 (M−H)−.

Workup

extractionthe mixture was extracted with ether (2×50 mL
extractionThe combined ethereal extract
washwashed with water, brine
dry with materialdried over Na2SO4
concentrationConcentration
customgave light brown oil, which
customwas purified by chromatography on a silica gel column
washeluted with a gradient from hexanes to 45% EtOAc

Sources & evidence

ORD record: ord-4495b9c45a3e46b2940804d57763387b
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569601B2

Reaction notes

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