Ethyl 3-(4-methoxybenzoyl)propionate → 4-(4-Hydroxyphenyl)-4-oxo-butyric acid ethyl ester

HRID 2042588Notes

Reaction equation

HRID 2042588 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=1)=[O:8])[CH3:2]>Br>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)=[O:8])[CH3:2]

Participants

3

Reactant 1

HCID 585132Ethyl 3-(4-methoxybenzoyl)propionate

Product 1

HCID 114359904-(4-Hydroxyphenyl)-4-oxo-butyric acid ethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
120 °C

Procedure

To 4-(4-methoxy-phenyl)-4-oxo-butyric acid ethyl ester (4.5 g, 19.0 mmol) was added 48% HBr (50 mL). After overnight stirring at 120° C., the reaction was concentrated and ethanol was added several times and concentrated to obtain 4.18 g product (94%); MS m/z 223 (M+H).

Workup

  1. concentrationthe reaction was concentrated
  2. additionethanol was added several times
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-605494865fdd47999234d57eead7d3e9
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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