Benzyltrimethylammonium hydroxide → 1-(2-Acetyl-3-hydroxyphenoxy)-2-hydroxy-3-m-cresyloxypropane

HRID 1606806Notes

Reaction equation

HRID 1606806 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)[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(OCCO)C>[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]=[C:14]([CH3:18])[CH:13]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 696872',6'-DihydroxyacetophenoneHCID 98180((m-Tolyloxy)methyl)oxirane

Product 1

HCID 215447821-(2-Acetyl-3-hydroxyphenoxy)-2-hydroxy-3-m-cresyloxypropaneYield 99.7%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 2,6-dihydroxyacetophenone (15.2 g), m-cresylglycidyl ether (16.4 g) and benzyltrimethylammonium hydroxide (10 drops of a 40% solution) in 2-ethoxyethanol (75 ml) was heated under reflux for 48 hours. The solvent was then removed under reduced pressure to give 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-m-cresyloxypropane (31.5 g) as a viscous amber oil.

Workup

  1. temperatureunder reflux for 48 hours
  2. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-2b1b1c294c094e47b786ad98c73911e8
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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