Acetone → 2-Hydroxy-4-(trifluoromethyl)benzaldehyde

HRID 2401699Notes

Reaction equation

HRID 2401699 reaction equation
C(OC[O:5][C:6]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])C.CC(C)=O.Cl>O>[OH:5][C:6]1[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 86680838HCID 86680838, compound

Product 1

HCID 224939012-Hydroxy-4-(trifluoromethyl)benzaldehydeYield 72.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1.90 g of 2-ethoxymethoxy-4-trifluoromethylbenzaldehyde, 10 ml of acetone, and 9 ml of 6 N hydrochloric acid was stirred at room temperature for 3 hours and subsequently at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, then water was added to the reaction mixture. This mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure, to obtain 1.05 g of 2-hydroxy-4-(trifluoromethyl)benzaldehyde.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThis mixture was extracted twice with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f89922f072549efae67753ae4381793
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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