Water → 4-Chloro-alpha-(trichloromethyl)benzenemethanol
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]([Cl:16])([Cl:15])C(O)=O.[Na+].ClC(Cl)(Cl)C([O-])=O.O>CN(C)C=O>[Cl:10][C:11]([Cl:16])([Cl:15])[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)[OH:7]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 32.5 °C
Procedure
A mixture of 4-chloro-benzaldehyde (35.5 g) and trichloro acetic acid (61.5 g) in N,N-dimethylformamide (200 ml) is stirred at 30-35° C. Trichloro acetic acid sodium salt (71.5 g) is added in portions over 20 minutes. Occasionally cooling is necessary. The reaction mixture is stirred at 30° C. for 2 hours. Towards the end it becomes viscous and additional N,N-dimethylformamide (150 ml) is charged. The reaction mixture is poured into water (700 ml). The aqueous phase is extracted with ethyl acetate (600 ml). The organic phase is separated, washed with water (300 ml), dried (magnesium sulfate) and evaporated. 2,2,2-Trichloro-1-(4-chloro-phenyl)-ethanol is obtained as oil.
Workup
- temperatureOccasionally cooling
- stirringThe reaction mixture is stirred at 30° C. for 2 hours
- extractionThe aqueous phase is extracted with ethyl acetate (600 ml)
- customThe organic phase is separated
- washwashed with water (300 ml)
- dry with materialdried (magnesium sulfate)
- customevaporated
Sources & evidence
- ORD record
- ord-01fa141735804517b7c8aab1b4b6387e
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129560B2
Reaction notes
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