Potassium Acetate → p-Methoxyphenylpropionic acid

HRID 2290950Notes

Reaction equation

HRID 2290950 reaction equation
Br[CH:2](C)[C:3](OC)(OC)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[C:17]([O-:20])(=[O:19])C.[K+]>CN(C)C=O.O>[CH3:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([CH:3]([CH3:2])[C:17]([OH:20])=[O:19])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 155798821-(2-Bromo-1,1-dimethoxypropyl)-4-methoxybenzene

Product 1

HCID 257576p-Methoxyphenylpropionic acid

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-bromo-1,1-dimethoxy-1-(4-methoxyphenyl)-propane (0.36 g; 1.25 mmol), potassium acetate (0.15 g; 1.5 mmol) and N,N-dimethylformamide:water (6:4 v/v) (3.5 ml) is heated at 95° C. under stirring for 22 h. Usual work up gives 2-(4-methoxyphenyl)-propionic acid. 2-(1-Bromoethyl)-2-(4-methoxyphenyl)-1,3-dioxolane (0.36 g; 1.25 mmol) and 2-chloro-1,1-dimethoxy-1-(4-methoxyphenyl)-propane (0.30 g; 1.25 mmol), when reacted, separately, under the reaction conditions above described give similar results.

Sources & evidence

ORD record
ord-b058b96aa94e46efb6a852dd19bc4d34
Source dataset
uspto-grants-1986_10
Patent number
US04618697

Reaction notes

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