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

HRID 2245192Notes

Reaction equation

HRID 2245192 reaction equation
[BH4-].[Na+].C(COC)OC.[C:9]([O:19][C:20]([C:26]([O:29][C:30]([C:36]([O:39][C:40]([C:46]([O:49][C:50]([C:56]([O:59][C:60]([C:66]([O:69][C:70]([C:76](OC)=[O:77])([C:72]([F:75])([F:74])[F:73])[F:71])([F:68])[F:67])([C:62]([F:65])([F:64])[F:63])[F:61])([F:58])[F:57])([C:52]([F:55])([F:54])[F:53])[F:51])([F:48])[F:47])([C:42]([F:45])([F:44])[F:43])[F:41])([F:38])[F:37])([C:32]([F:35])([F:34])[F:33])[F:31])([F:28])[F:27])([C:22]([F:25])([F:24])[F:23])[F:21])([C:12]([C:15]([F:18])([F:17])[F:16])([F:14])[F:13])([F:11])[F:10].Cl>O.CO>[C:9]([O:19][C:20]([C:26]([O:29][C:30]([C:36]([O:39][C:40]([C:46]([O:49][C:50]([C:56]([O:59][C:60]([C:66]([O:69][C:70]([CH2:76][OH:77])([C:72]([F:73])([F:74])[F:75])[F:71])([F:67])[F:68])([C:62]([F:63])([F:64])[F:65])[F:61])([F:58])[F:57])([C:52]([F:53])([F:54])[F:55])[F:51])([F:48])[F:47])([C:42]([F:45])([F:44])[F:43])[F:41])([F:38])[F:37])([C:32]([F:35])([F:34])[F:33])[F:31])([F:28])[F:27])([C:22]([F:25])([F:24])[F:23])[F:21])([C:12]([C:15]([F:18])([F:17])[F:16])([F:14])[F:13])([F:11])[F:10]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 80711,2-DimethoxyethaneHCID 4311764Sodium borohydrideHCID 131727987HCID 131727987, compound

Product 1

HCID 152195982,4,4,5,7,7,8,10,10,11,13,13,14,16,16,17,19,19,20,20,21,21,21-Tricosafluoro-2,5,8,11,14,17-hexakis(trifluoromethyl)-3,6,9,12,15,18-hexaoxahenicosan-1-olYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  1. customresulting in an exotherm
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-4d27030d58bb4a9eadc1cf716f66c8d4
Source dataset
uspto-grants-2010_03
Patent number
US07682771B2

Reaction notes

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