Isophthalaldehyde → 3-(Hydroxymethyl)benzaldehyde

HRID 1755779Notes

Reaction equation

HRID 1755779 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+].C([O-])(=O)C.[NH4+]>C(O)C>[OH:10][CH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 34777IsophthalaldehydeHCID 517165Ammonium AcetateHCID 4311764Sodium borohydride

Product 1

HCID 131314553-(Hydroxymethyl)benzaldehydeYield 46.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To isophthalaldehyde (200 g) in absolute ethanol (3 L) at 0° C. was added NaBH4 (15.6 g). After 1 hour at O° C. the reaction mixture was poured onto 25% aqueous ammonium acetate (2 L). The ethanol was evaporated and the product was extracted with EtOAc. The resulting mixture was purified by flash chromatography (30% EtOAc/Hexane) to provide 94 g of the title product.

Workup

  1. customThe ethanol was evaporated
  2. extractionthe product was extracted with EtOAc
  3. customThe resulting mixture was purified by flash chromatography (30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-11e98644f9bb4c2fbbfd03e72b778ad2
Source dataset
uspto-grants-1995_08
Patent number
US05438141

Reaction notes

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