Urea → p-Methoxyphenylpropionic acid

HRID 2290948Notes

Reaction equation

HRID 2290948 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.NC(N)=O.[C:21](=O)([O-:23])[O-:22].[Ca+2]>CN(C)C=O>[CH3:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([CH:3]([CH3:2])[C:21]([OH:23])=[O:22])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 10112Calcium CarbonateHCID 155798821-(2-Bromo-1,1-dimethoxypropyl)-4-methoxybenzene

Product 1

HCID 257576p-Methoxyphenylpropionic acidYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-bromo-1,1-dimethoxy-1-(4-methoxyphenyl)-propane (2.9 g; 10 mmol), N,N-dimethylformamide (13 g), urea (6 g) and calcium carbonate (1.2 g; 12 mmol) is heated at 95° C. under stirring for 32 h. The reaction mixture is worked up as described in example 1a to give 2-(4-methoxyphenyl)-propionic acid (1.7 g; 9.2 mmol; yield 92%), m.p. 56°-57° C.

Sources & evidence

ORD record
ord-c89712df2dde4a7c87acea05043ec11d
Source dataset
uspto-grants-1986_10
Patent number
US04618697

Reaction notes

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