Isophthalaldehyde → 3-(Hydroxymethyl)benzaldehyde

HRID 846447Notes

Reaction equation

HRID 846447 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1>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

3

Reactant 1

HCID 34777Isophthalaldehyde

Product 1

HCID 131314553-(Hydroxymethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of isophtalaldehyde (8 g) in ethanol (80 mL) at room temperature was added NaBH portion wise, until about 50% reaction by TLC. The reaction mixture was quenched with 25% ammonium acetate, extracted with ethyl acetate, which was washed with brine (2x), dried over sodium sulfate, filtered and evaporated to dryness. Purification of the residue by flash chromatography using 50% ether in hexane afforded the pure title compound.

Workup

  1. customuntil about 50% reaction by TLC
  2. customThe reaction mixture was quenched with 25% ammonium acetate
  3. extractionextracted with ethyl acetate, which
  4. washwas washed with brine (2x)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-0a744919107b4dbd884c7ced153257a9
Source dataset
uspto-grants-1992_08
Patent number
US05136034

Reaction notes

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