Isobutyraldehyde → Benzyl(2-methylpropyl)amine

Reaction equation

[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[CH2:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.P(O)(O)O>O>[CH2:6]([NH:13][CH2:1][CH:2]([CH3:4])[CH3:3])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Procedure

To the imine from isobutyraldehyde and benzylamine (51.4 g; 0.3 mole) was added phosphorous acid (24.6 g; 0.3 mole). While stirring the mixture was slowly warmed to 65°-70° when a vigorous exothermic reaction was initiated. The reaction temperature reached 130°-145°. Upon cooling the reaction mixture became a glass. This glass was dissolved in water and basified. Extraction with benzene yielded benzylisobutylamine. The aqueous portion was acidified and after removal of sodium chloride yielded a phosphonic acid (20 g). Recrystallization gave a white solid (12 g) mp 186°-190° the N-benzyl α-aminophosphonic acid. ##STR35##