Ethanol → 3-(Hydroxymethyl)benzaldehyde

HRID 2259488Notes

Reaction equation

HRID 2259488 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1.CCO.[BH4-].[Na+].CCOC(C)=O>C1COCC1>[OH:10][CH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 34777IsophthalaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 131314553-(Hydroxymethyl)benzaldehydeYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Isophthalaldehyde (150 g, 1.1 mole) was dissolved in THF (1 L) and EtOH (1 L) at 0° C. NaBH4 (11.0 g, 291 mmol) was added portionwise and the mixture stirred 1 hr at 0° C. Addition of 25% aq. NH4OAc and extraction with EtOAc (2×) followed by purification by flash chromatography (20%→40% EtOAc in hexanes) yielded 60 g of 3-(hydroxymethyl)-benzaldehyde.

Workup

  1. customat 0° C
  2. customfollowed by purification by flash chromatography (20%→40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-52b8eec7b2714c8cbac23fdd64b745c2
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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