Hydrochloric Acid → [4-(Trifluoromethyl)phenyl]acetaldehyde

HRID 1992382Notes

Reaction equation

HRID 1992382 reaction equation
C[O:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.Cl>CC(C)=O>[F:12][C:11]([F:13])([F:14])[C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH:3]=[O:2])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 538974091-Trifluoromethyl-4-(2-methoxyvinyl)benzene

Product 1

HCID 14298210[4-(Trifluoromethyl)phenyl]acetaldehydeYield 96.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 1-(2-methoxy-vinyl)-4-trifluoromethylbenzene (10.5 g, 0.052 mol, from step (i) above) in 158 ml acetone was added 107.3 ml 3 M HCl and stirred at 45° C. for 4 h. Acetone was evaporated under reduced pressure and the residue was partitioned between water and ether. Organic layer was washed with NaHCO3, brine and dried over sodium sulfate. Solvent evaporation under reduced pressure afforded the sub-title compound (9.4 g ) as pale yellow liquid. This was directly taken for next step without further purification.

Workup

  1. customAcetone was evaporated under reduced pressure
  2. customthe residue was partitioned between water and ether
  3. washOrganic layer was washed with NaHCO3, brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-0b00b598e3c34b96871992381edaab8d
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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