Hydrochloric Acid → HCID 53790038, compound

Participants

Reaction Steps

(2-Methoxy-4-formylphenoxy)acetic acid (10.5 g, 0.05 mole), butylamine (14.6 g, 0.2 mole) and benzene were united and refluxed in a flask equipped with a Dean-Stark water separator. The mixture was refluxed for 4 hours and then the benzene removed by distillation at reduced pressure. The residue consisted of 2-methoxy-4-(butyliminomethylene)-phenoxy)acetic acid which was treated with nitro-propane (17.8 g, 0.2 mole) and acetic acid (50 ml) and heated to boiling. After standing for 30 minutes the mixture was poured into crushed ice and acidified with hydrochloric acid. The solid that separated was removed by filtration, washed with water, dried and recrystallized first from a mixture of water and isopropyl alcohol (3:1) and then from a mixture of benzene and hexane (4:3) to give product melting at 116°-117° C.

Provenance & Evidence