Acetic Anhydride → N-{[2-(Methoxymethyl)phenyl]methyl}acetamide

HRID 981808Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][NH2:11].[C:12](OC(=O)C)(=[O:14])[CH3:13].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][NH:11][C:12](=[O:14])[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

604 g (4 moles) of o-aminomethylbenzyl methyl ether were dissolved in 1,500 ml of toluene, and 408 g (4 moles) of acetic anhydride were added to the stirred and cooled solution at a rate such that 60° C. was not exceeded. Stirring was continued, the mixture was neutralized with 424 g of 25% strength sodium hydroxide solution, and the aqueous phase was separated off. When the organic phase was evaporated down, 656 g (85% of theory) of the acylated benzyl ether of melting point 67°-68° C. crystallized.

Workup

stirringStirring
customthe aqueous phase was separated off
customWhen the organic phase was evaporated down
custom656 g (85% of theory) of the acylated benzyl ether of melting point 67°-68° C. crystallized

Sources & evidence

ORD record: ord-8bd428c8a26e4c96809bd7b9931101b5
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992588

Reaction notes

Loading…