Ethanol → 4-[1-(Acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]benzaldehyde

HRID 4743Notes

Reaction equation

HRID 4743 reaction equation
C(O)C.C([O:7][CH:8](OC(=O)C)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:24][C:25](=[O:27])[CH3:26])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)(=O)C.S(=O)(=O)(O)O>O>[C:25]([O:24][C:15]([C:12]1[CH:11]=[CH:10][C:9]([CH:8]=[O:7])=[CH:14][CH:13]=1)([C:16]([F:19])([F:18])[F:17])[C:20]([F:21])([F:23])[F:22])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14076668alpha,alpha-Bis-acetyloxy-4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]toluene

Product 1

HCID 201518544-[1-(Acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]benzaldehydeYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 130 ml of ethanol are added 60 g (0.15 mole) of α,α-bis-acetyloxy-4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]toluene and 13.5 ml of concentrated sulfuric acid in 135 ml of water. The resulting solution is stirred and heated at reflux for thirty minutes. The solution is then cooled and extracted with 1 liter of ether to obtain an ether solution which is washed with water and a saturated sodium bicarbonate solution until the washes were basic. The ether solution is dried with anhydrous magnesium sulfate, filtered and evaporated at reduced pressure to give 42 g of 4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]benzaldehyde. This compound was not further purified but was used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for thirty minutes
  3. temperatureThe solution is then cooled
  4. extractionextracted with 1 liter of ether
  5. customto obtain an ether solution which
  6. washis washed with water
  7. dry with materialThe ether solution is dried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-e7b09e39e6d0482c831f6c8380c5c8e2
Source dataset
uspto-grants-1988_02
Patent number
US04727180

Reaction notes

Loading…