Glycolic Acid → HCID 20274488, compound

Participants

Reaction Steps

4,9-Dioxadodecane-1,12-diamine (22.8 g, 0.112 mole) was placed in a 250 ml round bottom flask and glycolic acid (17.0 g, 0.224 mole) added portion-wise with stirring and cooling. The resultant liquid was heated in an oil bath to 185° C. whereupon distillation of water occurred. Heating was continued at 185° to 195° C. for 2 hours after which time distillation of water subsided and the liquid was poured into a crystallization dish. The resultant oil slowly crystallized in the form of large white clusters; yield 35.5 g (99.3%); m.p. 67°-71° C. The solid was recrystallized from cold absolute methanol to give a white, crystalline product; m.p. 74°-77° C.; infrared (Nujol), 1120 cm-1, 1625 cm-1, 3250 cm-1 ; proton nuclear magnetic resonance (CDCl3 /TMS, 100 MHz), δ1.55-1.95 (complex multiplet, 8 protons), δ3.30-3.65 (complex multiplet, 12 protons), δ4.03 (singlet, 4 protons), δ4.98 (broad singlet, 2 protons), δ7.51 (broad triplet, 2 protons).

Provenance & Evidence