Sodium Cyanide → 3-(Cyanomethyl)benzoic acid
Reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[C-:12]#[N:13].[Na+]>CO>[C:12]([CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])#[N:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 3-bromomethylbenzoic acid (2.29 g, 10 mmol) in methanol (30 mL) is added sodium cyanide (0.49 g, 10 mmol) and the mixture is stirred at 70° C. for 2 hrs. The solvent is removed under reduced pressure and water is added to the residue. The mixture is extracted with ether and the organic phase is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by column chromatography using CH2Cl2 as eluent to give 3-cyanomethylbenzoic acid.
Workup
- customThe solvent is removed under reduced pressure and water
- additionis added to the residue
- extractionThe mixture is extracted with ether
- dry with materialthe organic phase is dried over sodium sulfate
- customThe solvent is removed under reduced pressure
- customthe residue purified by column chromatography
Sources & evidence
- ORD record
- ord-4ef984e7f6424b388fcec863111b9a63
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263629B2
Reaction notes
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