1-Hexanol → Methanesulfonic acid, trifluoro-, hexyl ester

HRID 729051Notes

Reaction equation

HRID 729051 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16](O)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 81031-Hexanol3×HCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 10889835Methanesulfonic acid, trifluoro-, hexyl esterYield 47.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under a dry nitrogen atmosphere, a solution of 18.1 g (177 mmol) 1-hexanol (dried over 3A sieves) and 14.1 g (178 mmol) pyridine (dried over 3A sieves) in 80 mL carbon tetrachloride (dried over 3A sieves) was added over 1.25 hr to a solution of 50 g (180 mmol) trifluoromethanesulfonic anhydride in 50 mL dry carbon tetrachloride, while cooling in an ice-waterbath. After an additional 5 min, the mixture was filtered, and the solids were washed with cold carbon tetrachloride. The filtrate was evaporated, and the residue was distilled, giving 19.7 g (47.5%) of hexyl trifluoromethanesulfonate: bp 35°-36° C. (0.35-0.40 torr).

Workup

  1. filtrationthe mixture was filtered
  2. washthe solids were washed with cold carbon tetrachloride
  3. customThe filtrate was evaporated
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-f4a915d87bd7434083f7c3ffaaa908df
Source dataset
uspto-grants-1991_09
Patent number
US05051330

Reaction notes

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