Terephthalaldehyde → 4-(Hydroxymethyl)benzaldehyde

HRID 266670Notes

Reaction equation

HRID 266670 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H][H]>O.C(O)C.[Pd]>[OH:10][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 12173TerephthalaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 5563304-(Hydroxymethyl)benzaldehydeYield 99.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Terephthalaldehyde (25.0 g) was suspended in water (20 ml) and ethanol (80 ml). Pd/C (220 mg) was added to the suspension and then hydrogen gas (4.3 l ) was introduced. The catalyst was removed by filtration and the filtrate was concentrated to give p-hydroxymethylbenzaldehyde (25.2 g). The product was dissolved in toluene (100 ml) and 48% HBr (50 ml) and the solution was refluxed for 2 hours. The reaction mixture was poured into iced water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline and dried, and then the solvent was removed by evaporation under reduced pressure. The residue was recrystallized from n-hexane to give colorless needles (37.5 g, yield: 82%). mp 97.5°-98.0° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2d0919c636d64d17a288190345074958
Source dataset
uspto-grants-1997_07
Patent number
US05652232

Reaction notes

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