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Potassium Cyanide → alpha-Hydroxy-(4'-methylbiphenyl-2-yl)acetonitrile

HRID 2210583
Notes
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Reaction equation

HRID 2210583 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 13940094'-Methyl-[1,1'-biphenyl]-2-carbaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 19378952alpha-Hydroxy-(4'-methylbiphenyl-2-yl)acetonitrileYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 3283
Diethyl Ether
Solvent

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

  1. waitat 20° C. for 30 minutes
  2. extractionAt the end of this time, the product was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent was removed by evaporation under reduced pressure
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-e99d920c3f9f430cb463cef7d3151efa
Source dataset
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05459148

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes