4-Methoxybenzoic Acid → HCID 20371624, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methoxybenzoic acid (0.76 g, 0.0050 mole) and of triethyl amino (0.70 ml, 0.0050 mole) in dry acetone (8 ml) was cooled to -15° C and ethyl chloroformate (0.54 g, 0.0050 mole) was added dropwise. The mixture was stirred 30 minutes at -15° C, and 30 minutes at 0° C, and then cooled to -15° C. A solution of 3-amino-4-hydroxy-α-(tert.butylaminomethyl)benzylalcohol hydrochloride in acetone (10 ml) and water (1.7 ml) was cooled to -15° C and added to the reaction mixture in one portion. The solution obtained was stirred at -15° C for 30 minutes, at 0° C for 30 minutes, and at room temperature for 1 hour. The solution was evaporated in vacuum and the residue was recrystallized from water yielding 1.02 g (52%), m.p. 224°-225° C of the title compound, identical to the compound prepared in Example 5.

Provenance & Evidence