o-CRESYL GLYCIDYL ETHER → HCID 21544835, compound

HRID 1606801Notes

Reaction equation

HRID 1606801 reaction equation
[CH3:1][C:2]([C:4]1[C:5]([OH:11])=[CH:6][CH:7]=[CH:8][C:9]=1[OH:10])=[O:3].[C:12]1([O:19][CH2:20][CH:21]2[O:23][CH2:22]2)[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=1>C(OCCO)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[C:2]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH2:22][CH:21]([OH:23])[CH2:20][O:19][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])(=[O:3])[CH3:1]

Participants

5

Reactant 2

HCID 16640o-CRESYL GLYCIDYL ETHERHCID 696872',6'-Dihydroxyacetophenone

Product 1

HCID 21544835HCID 21544835, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 66854Benzyltrimethylammonium hydroxideCatalystHCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 2,6-dihydroxyacetophenone (15.2 g) and o-cresylglycidyl ether (16.4 g) in 2-ethoxyethanol (75 ml) containing benzyltrimethylammonium hydroxide solution (10 drops; 40%) was heated under reflux for 48 hours. Following removal of the 2-ethoxyethanol under reduced pressure, the resulting solid was washed with ether to give 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-o-cresyloxypropane (19.2 g) as a cream solid, m.p. 101°-102.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customremoval of the 2-ethoxyethanol under reduced pressure
  4. washthe resulting solid was washed with ether

Sources & evidence

ORD record
ord-3d1d0c96c644426db75167d6e7695d94
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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