Acetone → 2-(3-Benzyloxyphenoxy)ethanol

HRID 327647Notes

Reaction equation

HRID 327647 reaction equation
OCC[C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27](C)=[O:28]>>[C:13]1([CH2:12][O:11][C:10]2[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=2)[O:6][CH2:26][CH2:27][OH:28])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 21935072HCID 21935072, compound

Product 1

HCID 121470482-(3-Benzyloxyphenoxy)ethanolYield 92%

Procedure

A slurry of 38.6 g (0.25 mole) of o-(2-hydroxyethyl)resorcinol (Lancaster), 44.3 g (0.35 mole) of benzyl chloride, and 55.2 g (0.40 mole) of potassium carbonate in 200 ml of acetone was stirred and heated at reflux for 72 hr. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The crystalline residue was recrystallized from toluene/petroleum ether to give 56.3 g (92%) of the title compound as white flakes, mp 40.5°-43.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 72 hr
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe crystalline residue was recrystallized from toluene/petroleum ether

Sources & evidence

ORD record
ord-2c7d4540592e4aedbad4acd6cf4f480b
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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