Benzyl Alcohol → HCID 10662990, compound

Participants

Reaction Steps

A mixture of iminodiacetic acid (16.64 g, 0.125 mol), toluenesulfonic acid (28.5 g, 0.15 mol), and 60 ml of benzyl alcohol in 100 ml benzene was refluxed for 24 h with continuous removal of water using a Dean-Stark trap. After addition of ether to the cooled reaction mixture, toluenesulfonate salt of the benzylated iminodiacetate was obtained as a solid. Subsequently, triethylamine (25 ml) was added to a suspension of the toluenesulfonate salt in ethyl acetate and stirred for 30 minutes. The ethyl acetate solution was washed with water, dried with MgSO4, filtered and concentrated under reduced pressure affording 35.7 g (91%) of compound 1 used for the next reaction step without further purification. NMR (CDCl3):1.4-2.2 (br s,1H), 3.52 (s,4H), 7.35 (s,10H).

Provenance & Evidence