Lithium hydroxide, monohydrate → 4,4,4-Trifluorobutanoic acid

HRID 1975427Notes

Reaction equation

HRID 1975427 reaction equation
O.[OH-].[Li+].[F:4][C:5]([F:14])([F:13])[CH2:6][CH2:7][C:8]([O:10]CC)=[O:9]>O.CO.O1CCCC1>[F:4][C:5]([F:14])([F:13])[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 2733273Ethyl 4,4,4-trifluorobutyrate

Product 1

HCID 27770854,4,4-Trifluorobutanoic acidYield 95.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (324 g) in water (1.8 L) was added to a stirred solution of ethyl 4,4,4-trifluorobutyrate (436 g) in methanol (2.0 L) and dry tetrahydrofuran (2.0 L) and the suspension was stirred overnight. After the suspension was partially evaporated, the residue was diluted with water and washed with diethyl ether. The aqueous layer was acidified with 6M hydrochloric acid and extracted with diethyl ether. The combined extracts were washed (brine), dried (MgSO4), and filtered. The filtrate was evaporated and the residue distilled (bp 165°-168° C.) to give 4,4,4-trifluorobutyric acid (347 g, 95%); mp 27°-30° C.; partial NMR; (300 MHz, CDCl3): 2.33-2.57 (m, 2H, CF3CH2), 2.66 (t, 2H, CH2CO2H).

Workup

  1. customAfter the suspension was partially evaporated
  2. additionthe residue was diluted with water
  3. washwashed with diethyl ether
  4. extractionextracted with diethyl ether
  5. washThe combined extracts were washed (brine)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. distillationthe residue distilled (bp 165°-168° C.)

Sources & evidence

ORD record
ord-3603c0951569424e9b1bf86975f06302
Source dataset
uspto-grants-1994_02
Patent number
US05286740

Reaction notes

Loading…