Sulfuric Acid → 2-Trifluoromethylhexanoic acid

HRID 1763678Notes

Reaction equation

HRID 1763678 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([CH2:9][CH2:10][CH2:11][CH3:12])[C:4]([O:6]CC)=[O:5].S(=O)(=O)(O)O.[Cl-].[Na+]>>[F:1][C:2]([F:13])([F:14])[CH:3]([CH2:9][CH2:10][CH2:11][CH3:12])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 10443153Ethyl 2-trifluoromethylhexanoate

Product 1

HCID 157451932-Trifluoromethylhexanoic acidYield 86%

Procedure

Ethyl 2-trifluoromethylhexanoate (10.05 g.) was mixed with 50 ml. of concentrated sulfuric acid and warmed to 75° C. for 20 hours. After cooling, the acid was poured onto excess ice. The resulting mixture was saturated with sodium chloride, extracted with ether (3 × 100 ml.). The combined ether extracts were dried (MgSO4) and evaporated to give a residual oil which yielded 2-trifluoromethylhexanoic acid (7.50 g.) upon distillation, b.p. 80°-85°/2.8 mmHg.

Workup

  1. temperatureAfter cooling
  2. additionthe acid was poured onto excess ice
  3. extractionextracted with ether (3 × 100 ml.)
  4. dry with materialThe combined ether extracts were dried (MgSO4)
  5. customevaporated
  6. customto give a residual oil which

Sources & evidence

ORD record
ord-089be89b014a456488f4ea83ad87a332
Source dataset
uspto-grants-1978_09
Patent number
US04112225

Reaction notes

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