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

HRID 1385856Notes

Reaction equation

HRID 1385856 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

7

Reactant 4

HCID 80742-Chloroethyl vinyl etherHCID 8471TriethylamineHCID 143274-CyclohexylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 220116871-Cyclohexyl-4-[2-(ethenyloxy)ethoxy]benzene

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

In 300 ml of toluene, 83.1 g (0.5 mol) of p-cyclohexylphenol was dissolved, and then 150 g of 2-chloroethyl vinyl ether, 25 g of sodium hydroxide, 5 g of tetrabutylammonium bromide and 60 g of triethylamine were added thereto, followed by a reaction at 120° C. for 5 hours. The reaction solution was washed with water, and excess chloroethyl vinyl ether and toluene were removed by distillation. The resulting oil was purified by distillation under reduced pressure to obtain 4-cyclohexylphenoxyethyl vinyl ether.

Workup

  1. customfollowed by a reaction at 120° C. for 5 hours
  2. washThe reaction solution was washed with water, and excess chloroethyl vinyl ether and toluene
  3. customwere removed by distillation
  4. distillationThe resulting oil was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-f79c2e2862cf48299d8cfaaeb44f3d7b
Source dataset
uspto-grants-2001_07
Patent number
US06265135B1

Reaction notes

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