Terephthalaldehyde → 4-(Hydroxymethyl)benzaldehyde

HRID 1280231Notes

Reaction equation

HRID 1280231 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[OH:10][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12173TerephthalaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 5563304-(Hydroxymethyl)benzaldehydeYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 2.06 g of terephthalaldehyde and 20 ml of ethanol were placed in a reaction vessel, to which 0.15 g of sodium borohydride was slowly added with stirring under ice cooling. After stirring at room temperature for 12 hours, the ethanol was evaporated. The residue was poured into diluted hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 1.06 g (yield, 51%) of p-(hydroxymethyl)benzaldehyde.

Workup

  1. additionwas slowly added
  2. stirringAfter stirring at room temperature for 12 hours
  3. customthe ethanol was evaporated
  4. additionThe residue was poured into diluted hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed twice with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto give a crude product

Sources & evidence

ORD record
ord-3e312da4c4974e4884c6d02dce0b9a0d
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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