4-(Cyanomethyl)benzoic acid → 2-(4-(Hydroxymethyl)phenyl)acetonitrile

HRID 898534Notes

Reaction equation

HRID 898534 reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)#[N:2].[BH4-].[Na+].S([O-])(O)(=O)=O.[K+]>O1CCCC1.O>[OH:9][CH2:8][C:7]1[CH:11]=[CH:12][C:4]([CH2:3][C:1]#[N:2])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 2708714-(Cyanomethyl)benzoic acidHCID 516920Potassium bisulfateHCID 4311764Sodium borohydride

Product 1

HCID 109971832-(4-(Hydroxymethyl)phenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.17 g (32 mol) of CDl are added to a solution of 4.7 g (29 mol) of 4-cyanomethyl-benzoic acid in 250 mL of tetrahydrofuran and stirred until no more gas is given off. This reaction mixture is added dropwise to a solution of 3.29 g (87 mol) of sodium borohydride in 200 mL of water in such a way that the temperature does not exceed 30° C. The mixture is stirred for two hours and the reaction mixture is adjusted to pH 3-4 with potassium hydrogen sulphate solution. Then it is extracted with EtOAc, the organic phase is dried over magnesium sulphate and the solvent is separated off using the rotary evaporator.

Workup

  1. customdoes not exceed 30° C
  2. stirringThe mixture is stirred for two hours
  3. extractionThen it is extracted with EtOAc
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. customthe solvent is separated off
  6. customthe rotary evaporator

Sources & evidence

ORD record
ord-1e438757ce044198bf1959b2b24aea90
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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