Dimethylformamide → Methyl 4-Benzoyl-3-hydroxyphenoxyacetate

HRID 1493414Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 15.0 g (70.0 mmol) of 2,4-dihydroxybenzophenone, 10.7 g (70 mmol) of methyl bromoacetate, 19.3 g (0.14 mol) of potassium carbonate, and 125 ml of N,N-dimethylformamide is stirred at 25° C. for 18 hours. The reaction mixture is partitioned between diethyl ether and 0.5 N hydrochloric acid. Solids are removed by filtration, and the filtrate is dried over magnesium sulfate and concentrated. The concentrate is partially dissolved in diethyl ether, and solids are removed by filtration. The solid material is recrystallized from dichloromethane: 2-propanol to afford 13.7 g (69% yield) of the title compound, a pale yellow solid, mp 131°-4° C.

Workup

customThe reaction mixture is partitioned between diethyl ether and 0.5 N hydrochloric acid
customSolids are removed by filtration
dry with materialthe filtrate is dried over magnesium sulfate
concentrationconcentrated
dissolutionThe concentrate is partially dissolved in diethyl ether
customsolids are removed by filtration
customThe solid material is recrystallized from dichloromethane

Sources & evidence

ORD record: ord-7c11d4a2427e41058ea5fcbcb5819b06
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021478

Reaction notes

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