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Hydrochloric Acid → 3-Phenoxybenzyl 2-(3-chloro-4-hydroxyphenyl)-2-methylpropyl ether

HRID 619992
Notes
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Reaction equation

HRID 619992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:29])([CH3:28])[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)[CH:5]=[CH:6][C:7]=1[O:8]CC.[OH-].[K+].CN1CCN(C)C1=O.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:29])([CH3:28])[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:16]=2)[CH:5]=[CH:6][C:7]=1[OH:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 66611,3-Dimethyl-2-imidazolidinone2×HCID 14797Potassium HydroxideHCID 30671833-Chloro-4-ethoxyneophyl 3-phenoxybenzyl ether

Product 1

HCID 110580703-Phenoxybenzyl 2-(3-chloro-4-hydroxyphenyl)-2-methylpropyl etherYield 48.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

100 g of 3-phenoxybenzyl 2-(3-chloro-4-ethoxyphenyl)-2-methylpropyl ether and 25 g of 97% potassium hydroxide were added to 300 ml of 1,3-dimethyl-2-imidazolidinone (hereinafter referred to as DMI) and the mixture was stirred at 150° C. for 18 h. After cooling to room temperature, the mixture was poured into water and made acidic with a concentrated aqueous hydrochloric acid solution. After extraction with benzene, the benzene solution was washed with water and dried. Benzene was distilled off under reduced pressure and the obtained oily residue was purified according to a column chromatography (silica gel, developer: benzene) to obtain 45.6 g of 3-phenoxybenzyl 2-(3-chloro-4-hydroxyphenyl)-2-methylpropyl ether (m.p. 68° to 69° C.).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionAfter extraction with benzene
  3. washthe benzene solution was washed with water
  4. customdried
  5. distillationBenzene was distilled off under reduced pressure
  6. customthe obtained oily residue was purified

Sources & evidence

ORD record
ord-4cf53a3e63ca4e588829b05f7f826fd5
Source dataset
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04818525

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes