Hydrochloric Acid → 2,4,4,5,7,7,8,10,10,11,13,13,14,16,16,17,19,19,20,20,21,21,21-Tricosafluoro-2,5,8,11,14,17-hexakis(trifluoromethyl)-3,6,9,12,15,18-hexaoxahenicosan-1-ol

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 30 g NaBH4 (Aldrich), 50 mL HFE, and 400 mL dry dimethoxyethane was treated over 6 hours with 1000 g C3F7O(CF(CF3)CF2O)5CF(CF3)COOCH3, resulting in an exotherm, and the mixture was stirred at 50° C. overnight. After cooling, the mixture was cautiously treated with first 50 mL MeOH and then 75 mL 5% HCl, with the first few mL of HCl causing vigorous foaming. Addition of 300 mL water, filtration of some white solid at the interphase, and stripping the lower layer gave 931 g C3F7O(CF(CF3)CF2O)5CF(CF3)CH2OH. A solution of 322 g of this and 38.9 g diisopropylethylamine (Aldrich) in 150 mL HFE was treated dropwise with 25.0 g acryloyl chloride (Aldrich), forming a white solid. This was stirred overnight at 50° C., cooled, treated with 4 mL water, 5.0 g K2CO3, and 25 g silica gel, waiting about 2 hours between each addition. The mixture was filtered and stripped to give 297.5 g of HFPO-5-DHA.

Provenance & Evidence