Dichloromethane → (3-Isopropoxyphenyl)methanol

HRID 1510151Notes

Reaction equation

HRID 1510151 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(Cl)Cl>CO>[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

5

Reactant 3

HCID 6344Dichloromethane2×HCID 7129143-IsopropoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2759474(3-Isopropoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 1 molar solution of 3-isopropoxy benzaldehyde (102 g, 0.621 moles) in methanol (620 mL) cooled to 0° was added (slowly) sodium borohydride powder (25.8 g, 0.683 moles)-dissolved in a minimum of methylene chloride and passed through a plug of silica gel washing with more methylene chloride until the silica gel was free of the product. The eluent was stripped to an oil and pumped on high vacuum overnight.

Workup

  1. custompumped on high vacuum overnight

Sources & evidence

ORD record
ord-bb2baadfd4414e958c89bb400d2de812
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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