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

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]

Participants

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

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with benzene
washThe benzene solution was washed with water
customdried
customBenzene was evaporated under reduced pressure
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

Linked notes

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