Phenyl glycidyl ether → 1-Phenoxy-2-propanol

HRID 1606792

Reaction equation

HRID 1606792 reaction equation
CC(C1C(O)=CC=CC=1O)=O.[C:12]1([O:18][CH2:19][CH:20]2[O:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(OCCO)C>[OH:22][CH:20]([CH2:19][O:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:21]

Participants

5

Reactant 3

HCID 31217Phenyl glycidyl etherHCID 66854Benzyltrimethylammonium hydroxideHCID 696872',6'-Dihydroxyacetophenone

Product 1

HCID 928391-Phenoxy-2-propanol

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 2,6-dihydroxyacetophenone (15.2g.), phenylglycidyl ether (15.0 g) and benzyltrimethylammonium hydroxide (5 drops of a 40% solution) in 2-ethoxyethanol (75 ml) was heated under reflux for 48 hours. The solvent was removed under reduced pressure and the resulting solid was washed with ether. Recrystallization from aqueous ethanol gave 1-(2-acetyl-3-hydroxyphenoxy(-2-hydroxy-3-phenoxypropane, 19.0 g, as pale lemon needles, m.p. 100.5°-101.5° C.

Workup

  1. temperatureunder reflux for 48 hours
  2. customThe solvent was removed under reduced pressure
  3. washthe resulting solid was washed with ether
  4. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-4c190907babd413c942a9bdef2d33127
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Linked notes

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