4-Formylbenzoic acid → 4-(Hydroxymethyl)benzoic acid

HRID 1110413Notes

Reaction equation

HRID 1110413 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:4]>O.[OH-].[Na+].C(O)C>[OH:4][CH2:3][C:5]1[CH:6]=[CH:7][C:8]([C:9]([OH:11])=[O:10])=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 120884-Formylbenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 763604-(Hydroxymethyl)benzoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3.68 g (92.3 mmol) of sodium borohydride, dissolved in 30 ml of water to which 5 ml of 5N NaOH have been added, is added dropwise and with stirring to a solution of 13.86 g (92.3 mmol) of 4-formylbenzoic acid in 200 ml of absolute ethanol. The reaction medium is left thus for 5 hours with stirring at room temperature. The ethanol is then removed by evaporation under vacuum and the residue is taken up with water and then acidified with 5N hydrochloric acid: the precipitate obtained is separated by filtration on a sinter.

Workup

  1. additionhave been added
  2. additionis added dropwise
  3. customThe ethanol is then removed by evaporation under vacuum
  4. customthe precipitate obtained
  5. customis separated by filtration on a sinter

Sources & evidence

ORD record
ord-a688355b03d84b91bd1d199a72ff215c
Source dataset
uspto-grants-1990_12
Patent number
US04975455

Reaction notes

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