4-Hydroxybenzyl Alcohol → (4-propoxyphenyl)methanol

HRID 1169447Notes

Reaction equation

HRID 1169447 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 78401-BromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 347843(4-propoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture (50 ml) of 4-hydroxybenzyl alcohol (1.5 g), 1-bromopropane (1.3 ml), potassium carbonate (2.5 g) and acetone (50 ml) was stirred at 60° C. for 8 hours. After concentration under reduced pressure, the residue was mixed with water and was extracted with ethyl acetate. The organic layer was washed with a 1N aqueous solution of sodium hydroxide and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. The resulting organic layer was concentrated under reduced pressure to obtain 4-propoxybenzyl alcohol (1.37 g) as a yellow oily substance.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. additionthe residue was mixed with water
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with a 1N aqueous solution of sodium hydroxide
  5. dry with materialan aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate
  6. concentrationThe resulting organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-42d2ea31c76249ee815153666574d6fb
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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