3-Hydroxybenzyl alcohol → (3-Isopropoxyphenyl)methanol

HRID 2167120Notes

Reaction equation

HRID 2167120 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([CH3:19])[CH3:18]>CN(C=O)C>[CH:17]([O:9][C:5]1[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[CH:7][CH:6]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 63582-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 2759474(3-Isopropoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 3-(hydroxymethyl)phenol (10 g) and potassium carbonate (27.2 g) in DMF (100 ml) was added 2-bromo-propane (14.8 g), the reaction was heated to 90° C. overnight. The reaction mixture was filtered and the filtrate was concentrated and purified by chromatography on silica gel, eluting with petrol:ethyl acetate=5:1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by chromatography on silica gel
  4. washeluting with petrol

Sources & evidence

ORD record
ord-447d2a63db3a4f71ba6705e136bed95b
Source dataset
uspto-grants-2015_06
Patent number
US09044463B2

Reaction notes

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