1,3-Dichloropropane → Trimethylene glycol di-p-aminobenzoate

Participants

Reaction Steps

Japanese Kokai 58059949 A2 discloses the preparation of 1,3-propanediol-bis(p-aminobenzoate) by heating Cl(CH2)3R (R=Cl, Br) with sodium or potassium p-aminobenzoate in an aprotic dipolar solvent, e.g., dimethyl formamide, dimethyl sulfoxide, or N-methylpyrrolidone. Thus, 0.15 mol of Cl(CH2)3Cl was heated with 0.3 mol sodium p-aminobenzoate in dimethyl sulfoxide at 100° for three hours to give 91.5 percent 1,3-propanediol bis(p-aminobenzoate) of 97.4 percent purity as opposed to a 3 percent yield with ethylene glycol as solvent. Cl(CH2)nCl(n=2, 4, 5, 8), instead of Cl(CH2)3Cl, gave the corresponding alkylene bis(p-aminobenzoates) in much lower yield.

Provenance & Evidence