Formamide → p-Methoxyphenylpropionic acid

HRID 2290946Notes

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+].C(N)=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

Reactant 3

HCID 713Formamide

HCID 517044Potassium Acetate

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

Product 1

HCID 257576p-Methoxyphenylpropionic acidYield 4,960%

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-bromo-1,1-dimethoxy-1-(4-methoxyphenyl)-propane (3.6 g; 13 mmol), potassium acetate (2.5 g; 0.25 mmol) and formamide (25 ml) is heated at 95° C. under stirring for 6 h. The reaction mixture is worked up as described in example 1a to give 2-(4-methoxyphenyl)-propionic acid (2.2 g; 12.4 mmol; yield 96%), m.p. 56°-57° C.

Sources & evidence

ORD record: ord-4ff1e02025bf499fba877c57c2dbe2f4
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04618697

Reaction notes

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