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rac 1-Lauroyl-3-chloropropanediol synthesis

2synthesis methods
-

Yield:20542-96-5 80%

Reaction Conditions:

with tetrabutylammomium bromide in ethanol at 85; for 15 h;

Steps:

Synthesis of 3-alkyl Acyloxy-2-hydroxy Chloropropane

General procedure: 30 mmollauric acid (6.01 g)/ myristic acid (6.85 g)/palmitic acid (7.70 g)/ stearic acid (8.53 g) and 0.3mmol(0.10 g) tetrabutylammonium bromide (TBAB) were dissolvedin 35 mL ethanol in a 100 mL round flask. 4 mL(4.72 g, 51mmol) epichlorohydrin was added drop wise intothe flask under 85 oC. The reaction solution was kept for 15h and stopped when the acid value of fatty acid was <1 mgKOH. Excess ethanol was removed under vacuum and theresidue was washed by distilled hot water three times. Waterwas removed under vacuum. The product was obtained in80% yield and was used for next synthesis without furtherpurified.

References:

Yu, Erlei;Mamat, Xamxikamar;Zhang, Yagang;Eli, Wumanjiang [Letters in Organic Chemistry,2015,vol. 12,# 8,p. 591 - 597]