2-Chloroethyl vinyl ether → 1-Cyclohexyl-4-[2-(ethenyloxy)ethoxy]benzene

HRID 1530154Notes

Reaction equation

[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:14]([O:16][CH2:17][CH2:18]Cl)=[CH2:15].[OH-].[Na+].C(N(CC)CC)C>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:14]([O:16][CH2:17][CH2:18][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:12][CH:11]=1)=[CH2:15]

Participants

Conditions

Temperature: 120 °C

Procedure

p-Cyclohexylphenol (83.1 g (0.5 mol)) was dissolved in 300 ml of toluene, and 150 g of 2-chloroethyl vinyl ether was added thereto. Furthermore, 25 g of sodium hydroxide, 5 g of tetrabutylammonium bromide and 60 g of triethylamine were added, and the resulting mixture was heated with stirring at 120° C. for 5 hours. The reaction solution was washed with water, and excess chloroethyl vinyl ether and toluene were removed by distillation under reduced pressure. From the obtained oil, the objective p-cyclohexylphenoxyethyl vinyl ether (X-1) was obtained by distillation under reduced pressure.

Workup

temperaturethe resulting mixture was heated
washThe reaction solution was washed with water, and excess chloroethyl vinyl ether and toluene
customwere removed by distillation under reduced pressure

Sources & evidence

ORD record: ord-9a25d57c76dd446f8ce17c907f969ed5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090722B2

Reaction notes

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