Water → p-Methoxyphenylpropionic acid

HRID 2290949Notes

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.CN1C[CH2:22][O:21]CC1.[OH2:24]>>[CH3:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([CH:3]([CH3:2])[C:22]([OH:21])=[O:24])=[CH:9][CH:8]=1

Participants

Reactant 3

HCID 962Water

HCID 79724-Methylmorpholine2×

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

Product 1

HCID 257576p-Methoxyphenylpropionic acidYield 96%

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-bromo-1,1-dimethoxy-1-(4-methoxyphenyl)-propane (2.8 g; 10 mmol), N-methylmorpholine (24 ml) and water (16 ml) is heated at 95° C., under stirring for 9 h. The reaction mixture is worked up as described in example 1a to give 2-(4-methoxyphenyl)-propionic acid (1.79 g; 9.6 mmol; yield 96%), m.p. 56°-57° C. (In this experiment, N-methyl-morpholine acts as weak base as well as dipolar aprotic diluent).

Sources & evidence

ORD record: ord-495249db13de475db9e799084137dffc
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04618697

Reaction notes

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