Benzaldehyde → 4-METHOXYBENZOIN

HRID 1460888Notes

Reaction equation

[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1>>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]([CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:8])=[O:16])=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 240Benzaldehyde

HCID 312444-Methoxybenzaldehyde

Product 1

HCID 37914-METHOXYBENZOIN

Procedure

Compounds of the invention having the formula ##STR19## can be prepared as follows. Benzaldehyde and 4-methoxybenzaldehyde are reacted to yield 4-methoxybenzoin, which is converted to the hemisuccinate by reaction with succinic anhydride. The latter is reacted with urea and acetic acid to yield the intermediate 4-(4-methoxyphenyl)-5-phenyl-2-oxazole-propionic acid. ##STR20## The latter intermediate is demethylated with hydrogen bromide and esterified with methanol to yield the corresponding hydroxy methyl ester intermediate, which is then reacted with an appropriate haloalky-A compound, where A is as defined hereinbefore and hal is halo, to yield the desired final product as the methyl ester. ##STR21## The ester can be hydrolyzed by conventional methods to yield the desired final product in its free carboxylic acid form.

Workup

customcan be prepared

Sources & evidence

ORD record: ord-e3d8a99f491848139c60a7d1b38b3f22
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05071988

Reaction notes

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