3-Isopropoxybenzaldehyde → (3-Isopropoxyphenyl)methanol

HRID 1780883Notes

Reaction equation

HRID 1780883 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][OH:9])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7129143-IsopropoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2759474(3-Isopropoxyphenyl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To m-isopropoxybenzaldehyde (38 g, 0.23 mol) in 500 mL of ethanol was added slowly sodium borohydride (12.2 g, 0.32 mol) over a period of 1 h and the mixture was stirred for 2 h, filtered, and concentrated to 100 mL of its volume. The above mixture was diluted with 50 mL of water, neutralized with sulfuric acid solution with cooling, and was extracted with ether (4×100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 36.32 g (95%) of m-isopropoxybenzyl alcohol.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to 100 mL of its volume
  3. additionThe above mixture was diluted with 50 mL of water
  4. temperaturewith cooling
  5. extractionwas extracted with ether (4×100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b39041356844f978eeaf41ddbba0159
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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