Methyl 2-(cyanomethyl)benzoate → (2-Hydroxymethylphenyl)acetonitrile

HRID 660800Notes

Reaction equation

HRID 660800 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]#[N:12].[Li+].[BH4-]>C1COCC1>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]#[N:12]

Participants

4

Reactant 2

HCID 588805Methyl 2-(cyanomethyl)benzoateHCID 4148881Lithium borohydride

Product 1

HCID 582335(2-Hydroxymethylphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-cyanomethylbenzoic acid methyl ester (1.75 g, 10 mmol) in THF (15 mL) is added LiBH4 (660 mg, 30 mmol) and the mixture is stirred at RT for 3 h. The mixture is quenched with MeOH then water is added. The mixture is extracted with EtOAc and the organic phase is washed with 1N HCl and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound which is used directly in the next step.

Workup

  1. customThe mixture is quenched with MeOH
  2. additionwater is added
  3. extractionThe mixture is extracted with EtOAc
  4. washthe organic phase is washed with 1N HCl and brine
  5. dry with materialthen is dried over magnesium sulfate
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-751a2c38adcd47debaa52e809b3b70a9
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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