Isophthalaldehyde → 3-(Hydroxymethyl)benzaldehyde

HRID 2242358Notes

Reaction equation

HRID 2242358 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1.[BH4-].[Na+]>CCO>[OH:10][CH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 34777IsophthalaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 131314553-(Hydroxymethyl)benzaldehydeYield 64.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of isophthalaldehyde (1.77 g, 13.0 mmol) in EtOH (30 ml) at 0° C., was added sodium borohydride (135 mg, 3.5 mmol). The reaction was stirred at 0° C. for 1 h. The solvent was evaporated and the residue purified by silica chromatography using DCM followed by DCM:MeOH (19:1) to yield 3-hydroxymethyl-benzaldehyde (1.14 g, 64%) as a yellow oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by silica chromatography

Sources & evidence

ORD record
ord-844fed8d6c2f41cabffb28add440ea40
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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