4-Hydroxybenzaldehyde → HCID 3609106, compound

Participants

Reaction Conditions

Reaction Steps

Propylamine (4.13 g) was slowly added to 4-hydroxybenzaldehyde (11.2 g, 91.80 mmol) in 50 mL of isopropanol at ambient temperature. The reaction was stirred for 1 hour and then cooled in an ice bath to 0° C. The imine was then reduced with sodium borohydride (1.74 g, 46 mmol) for 1 hour. The reaction was diluted with 100 mL of ethanol and acidified with acetic acid. The resulting solid was filtered and recrystallized from ethanol/isopropanol to give 15.1 g (99%) of the title compound. TLC (3:1 ethyl acetate/ethanol, trace triethylamine) Rf =0.37.

Provenance & Evidence