Sodium Cyanide → 3-(Cyanomethyl)benzoic acid

HRID 1469667Notes

Reaction equation

HRID 1469667 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

HCID 8929Sodium CyanideHCID 2456503-(Bromomethyl)benzoic acid

Product 1

HCID 155208513-(Cyanomethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customThe solvent is removed under reduced pressure and water
  2. additionis added to the residue
  3. extractionThe mixture is extracted with ether
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-b55156c7615f4664a42f381960f2562c
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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