Sodium Cyanide → HCID 20065474, compound
Reaction equation
Cl[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:3].[C-:14]#[N:15].[Na+]>CS(C)=O>[C:14]([CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]([CH3:12])[CH3:13])[CH3:3])#[N:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Crude 1-chloro-1-(isobutylphenyl)ethane containing 47g of 1-chloro-1-(isobutylphenyl)ethane was added to a mixture of 17g of sodium cyanide in 126g of dimethyl sulfoxide (DMSO). The reaction mixture was heated to 80° C. with agitation for 10 hours, after which the DMSO and inorganic salts were removed by water washing to yield 1-cyano-1-(isobutylphenyl)ethane. The crude nitrile was reacted with excess 50% sodium hydroxide at 135.C for four hours to form the sodium salt of 2-(isobutylphenyl)propionic acid, which was then acidified and crystallized from hexane at -10.C. The para/ortho ratio of the resultant 2-(isobutylphenyl)propionic acid in hexane solution was approximately 200/1.
Workup
- customafter which the DMSO and inorganic salts were removed by water washing
Sources & evidence
- ORD record
- ord-618dff91781d4e568bc80ee493336669
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05001288
Reaction notes
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