Methyl 4-Formylbenzoate → Methyl 4-(hydroxymethyl)benzoate

HRID 2259453Notes

Reaction equation

HRID 2259453 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=[O:2].[H][H]>[Ni].C1(C)C=CC=CC=1>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 81325Methyl 4-(hydroxymethyl)benzoateYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-formylbenzoate (500 g, 3.05 mole), Raney nickel (25 g) and toluene (1000 mL) is heated in an autoclave between 60 and 75° C. under a hydrogen atmosphere at between 41 and 44 bars absolute for 3.5 hours. The hydrogen pressure then is released and the catalyst removed from the reaction mixture by filtration at 40° to 60° C. The toluene is removed by distillation and the product, methyl 4-(hydroxymethyl)benzoate obtained in a 90% yield, is used in the next step without further purification.

Workup

  1. temperatureis heated in an autoclave between 60 and 75° C. under a hydrogen atmosphere at between 41 and 44 bars absolute for 3.5 hours
  2. customthe catalyst removed from the reaction mixture by filtration at 40° to 60° C
  3. customThe toluene is removed by distillation

Sources & evidence

ORD record
ord-2f6c1a8d86404fe798825fc663ea6604
Source dataset
uspto-grants-1995_12
Patent number
US05473098

Reaction notes

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