Sulfuric Acid → 2-Difluoromethoxy-alpha-cyano-benzyl alcohol
Reaction equation
[C-:1]#[N:2].[K+].[F:4][CH:5]([F:15])[O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].OS(O)(=O)=O>O.C(O)C>[F:4][CH:5]([F:15])[O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]([OH:10])[C:1]#[N:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
7.2 g of potassium cyanide were dissolved in 30 ml of water and 6 ml of ethanol, while cooling. 16 g of 2-difluoromethoxybenzaldehyde were then added at 0°-5° C., while cooling. After subsequently stirring the mixture between 0° and 10° C. for 20 minutes, a mixture of 7 ml of concentrated H2SO4 and 18 ml of water was added dropwise. The mixture was subsequently stirred for a further 2 hours and was thereby allowed to come to room temperature. After extracting twice with methylene chloride, the organic phase was dried and the solvent was distilled off. 2-Difluoromethoxy-α-cyano-benzyl alcohol was obtained as a colorless oil, the structure of which was confirmed by a nuclear magnetic resonance spectrum. The yield was virtually quantitative.
Workup
- temperaturewhile cooling
- additionwas added dropwise
- stirringThe mixture was subsequently stirred for a further 2 hours
- customto come to room temperature
- extractionAfter extracting twice with methylene chloride
- customthe organic phase was dried
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-4a7cb2ef83c94d33bcd4374a9854afa8
- Source dataset
- uspto-grants-1982_01
- Patent number
- US04310540
Reaction notes
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