Hydrochloric Acid → 4-(3,3,3-Trifluoropropoxy)benzoic acid

HRID 339511Notes

Reaction equation

HRID 339511 reaction equation
[OH-:1].[K+].[F:3][C:4]([F:17])([F:16])[CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.OO.Cl>CO>[F:3][C:4]([F:16])([F:17])[CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]([OH:1])=[O:13])=[CH:10][CH:9]=1

Participants

6

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 50% w/v KOH (0.8 ml) and 4-(3,3,3-trifluoropropoxy)benzaldehyde (0.4 g, 1.83 mmol) in MeOH (4 ml) at 65° C. was added dropwise over 20 min aqueous hydrogen peroxide (30 wt. % in water, 1.5 ml). On completion of the addition the reaction mixture was heated at 65° C. for a further 10 min. On cooling to room temperature, the reaction mixture was acidified with 1 M HCl and extracted with Et2O (3×25 ml). The combined organic extracts were washed with brine (25 ml), dried (Na2SO4) and the solvent removed under reduced pressure to give the title compound (0.36 g, 83%) as a colourless solid which was used without further purification.

Workup

  1. customat 65° C.
  2. additionOn completion of the addition the reaction mixture
  3. temperatureOn cooling to room temperature
  4. extractionextracted with Et2O (3×25 ml)
  5. washThe combined organic extracts were washed with brine (25 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3ddbd9232e7c4b4c9a40e16e6fa7bf6c
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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