Potassium Cyanide → α-Hydroxy-4′-methyl[1,1′-biphenyl]-2-acetonitrile
Reaction equation
[C-:1]#[N:2].[K+].S([O-])(O)=O.[Na+].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([CH:22]=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1>O.C(OCC)C>[OH:23][CH:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[CH:15][CH:14]=1)[C:1]#[N:2]Participants
Procedure
A solution of 6.0 g of potassium cyanide dissolved in 6 ml of water and a solution of 14 g of sodium hydrogensulfite dissolved in 35 ml of water were added dropwise at 0° to 5° C. to a solution of 8.00 g of 4'-methylbiphenyl-2-carbaldehyde (prepared as described in Preparation 1) dissolved in 10 ml of diethyl ether, and the resulting mixture was stirred at 5° to 10° C. for 3 hours and then at 20° C. for 30 minutes. At the end of this time, the product was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, after which the solvent was removed by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through silica gel, using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent, to give 7.7 g of the title compound as an oil.
Workup
- waitat 20° C. for 30 minutes
- extractionAt the end of this time, the product was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customafter which the solvent was removed by evaporation under reduced pressure
- additionby volume mixture of ethyl acetate and hexane as the eluent
Sources & evidence
- ORD record
- ord-e99d920c3f9f430cb463cef7d3151efa
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05459148
Reaction notes
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