Water → Methyl 3-{4-[(4-hydroxyphenyl)carbonyl]phenyl}propanoate

HRID 2100142Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:13][CH:12]=2)=[O:10])=[CH:5][CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>C1C=CC=CC=1>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of methyl 3-(4-{[4-(methyloxy)phenyl]carbonyl}phenyl)propanoate (167) (0.45 g, 1.51 mmol) and AlCl3 (0.82 g, 6.03 mmol) were refluxed in benzene (20 mL) for 1 h and then cooled to 0° C. in an ice bath. Water (15 mL) was added slowly, and the mixture was extracted with ether (2×50 mL). The combined ethereal extract was 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 0.41 g (96%) of the title compound 168 as colorless oil. 1H NMR (400 MHz, CDCl3): δ 2.68 (t, J=7.7 Hz, 2H), 3.03 (t, J=7.7 Hz, 2H), 3.68 (s, 3H), 5.44 (s, 1H), 6.89 (d, J=8.7 Hz, 2H), 7.30 (d, J=8.1 Hz, 2H), 7.69 (d, J=8.1 Hz, 2H), 7.77 (d, J=8.8 Hz, 2H). LCMS (ESI): m/z 285 (M+H)+, m/z 283 (M−H)−.

Workup

extractionthe mixture was extracted with ether (2×50 mL)
extractionThe combined ethereal extract
washwas washed 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-85396a1e636d45b896ec1bb42ab37ec7
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569601B2

Reaction notes

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