Sodium Hydroxide → Phenol, 4-(1,1-dimethyl-2-((3-phenoxyphenyl)methoxy)ethyl)-

HRID 619993Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:9]([CH3:27])([CH3:26])[CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[OH-].[Na+]>[Pd].CO>[OH:8][C:7]1[CH:2]=[CH:3][C:4]([C:9]([CH3:27])([CH3:26])[CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:14]=2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

20.0 g of 3-phenoxybenzyl 2-(3-chloro-4-hydroxyphenyl)-2-methylpropyl ether prepared in the above step (1), 2.67 g of 95% sodium hydroxide and 1.0 g of 5% Pd-C (50% hydrous) were added to 100 ml of 80% methanol and the mixture was stirred at 100° C. under a hydrogen pressure of 20 to 30 kg/cm2G for 6 h. After cooling, the catalyst was removed by filtration and the catalyst was washed thoroughly with benzene. The solvent was distilled off under reduced pressure. A dilute aqueous hydrochloric acid solution was added to the distillation residue. After extraction with benzene, the benzene solution was washed with water and dried. Benzene was distilled off under reduced pressure to obtain 18.2 g of intended 3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether (m.p. 69.2° to 70.0° C.).

Workup

temperatureAfter cooling
customthe catalyst was removed by filtration
washthe catalyst was washed thoroughly with benzene
distillationThe solvent was distilled off under reduced pressure
additionA dilute aqueous hydrochloric acid solution was added to the distillation residue
extractionAfter extraction with benzene
washthe benzene solution was washed with water
customdried
distillationBenzene was distilled off under reduced pressure

Sources & evidence

ORD record: ord-7a29f7acb0ec4f2f8a957c1b50d0d18d
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04818525

Reaction notes

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