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

HRID 2231339
Notes
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Reaction equation

HRID 2231339 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-imidazolidinoneHCID 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 962
Water
Solvent

Conditions

Temperature
150 °C

Procedure

One hundred grams of 3-phenoxybenzyl 2-(3-chloro-4-ethoxyphenyl)-2-methylpropyl ether and 25 g of potassium hydroxide were added to 300 ml of 1,3-dimethyl-2-imidazolidinone (to be abbreviated as DMI hereinafter), and the mixture was stirred at 150° C. for hours. The reaction mixture was cooled to room temperature, poured into water, acidified with a concentrated hydrochloric acid, and extracted with benzene. The benzene solution was washed with water, and dried. Benzene was evaporated under reduced pressure. The resulting oily residue was purified by column chromatography (silica gel; eluent: benzene) to give 45.6 g 3-phenoxybenzyl 2-(3-chloro-4-hydroxyphenyl)-2-methylpropyl ether having a melting point of 68° to 69° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with benzene
  3. washThe benzene solution was washed with water
  4. customdried
  5. customBenzene was evaporated under reduced pressure
  6. customThe resulting oily residue was purified by column chromatography (silica gel; eluent: benzene)

Sources & evidence

ORD record
ord-70c81f49e2d8426e8d2edacebf1895b2
Source dataset
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04782094

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes