Water → 3,5-Dimethyl-2-(2-propen-1-yl)-phenyl difluoromethyl ether

HRID 277672Notes

Reaction equation

[OH-].[Na+].[CH3:3][C:4]1[C:5]([CH2:12][CH:13]=[CH2:14])=[C:6]([OH:11])[CH:7]=[C:8]([CH3:10])[CH:9]=1.Cl[CH:16]([F:18])[F:17].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[F:17][CH:16]([O:11][C:6]1[CH:7]=[C:8]([CH3:10])[CH:9]=[C:4]([CH3:3])[C:5]=1[CH2:12][CH:13]=[CH2:14])[F:18]

Participants

Conditions

Temperature: 90 °C

Procedure

125 g of 45% strength sodium hydroxide solution and 10 g of tetrabutyl-ammonium bromide were metered into 100 g of 3,5-dimethyl-2-(2-propen-1-yl)-phenol (C) in 700 ml of toluene. The mixture was heated to 90° C., and 110 g of chlorodifluoromethane were subsequently passed in. After the mixture had cooled to room temperature, 300 ml of water were added, and the toluene phase was separated off. The aqueous phase was extracted twice using 200 ml of tert-butyl methyl ether, and the combined organic phases were dried over sodium sulphate. The mixture was concentrated, and, after distillation, 58.5 g (45% of theory) of 3,5-dimethyl-2-(2-propen-1-yl)-phenyl difluoromethyl ether of a boiling point of 55-65° C. at 0.15 mbar were obtained.

Workup

temperatureAfter the mixture had cooled to room temperature
customthe toluene phase was separated off
extractionThe aqueous phase was extracted twice
dry with materialthe combined organic phases were dried over sodium sulphate
concentrationThe mixture was concentrated
distillationafter distillation, 58.5 g (45% of theory) of 3,5-dimethyl-2-(2-propen-1-yl)-phenyl difluoromethyl ether of a boiling point of 55-65° C. at 0.15 mbar
customwere obtained

Sources & evidence

ORD record: ord-16529654b71547b08d0330111bf2c32a
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358887B1

Reaction notes

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