Phenyl glycidyl ether → HCID 18915770, compound

HRID 1292588Notes

Reaction equation

HRID 1292588 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[C:13]([C:17]([CH3:21])([CH3:20])[CH2:18][CH3:19])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:23]1[O:25][CH2:24]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH2:24][CH:23]([OH:25])[CH2:22][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:13]([C:17]([CH3:20])([CH3:21])[CH2:18][CH3:19])=[CH:12][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5]

Participants

5

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 18915766HCID 18915766, compound

Product 1

HCID 18915770HCID 18915770, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 10 g (35 mmol) of 2,4-dihydroxy-5-(1,1-dimethylpropyl)benzophenone, 5.8 g (38 mmol) of phenyl glycidyl ether, 1.3 g (3.5 mmol) of ethyltriphenylphosphonium bromide in 30 ml of xylene is stirred at 135° C. for 3 h. The reaction mixture is cooled and then filtered over Prolith rapid bleaching earth. The residue which remains after concentrating by evaporation is distilled in a bulb tube (250° C./0.1 mbar). 10.5 g (69%) of the compound are obtained as a viscous yellow liquid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered over Prolith rapid bleaching earth
  3. concentrationafter concentrating by evaporation
  4. distillationis distilled in a bulb tube (250° C./0.1 mbar)

Sources & evidence

ORD record
ord-7220ef667c834580b73dd3e7da384f1a
Source dataset
uspto-grants-1998_05
Patent number
US05756793

Reaction notes

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