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

HRID 658966

Reaction equation

HRID 658966 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 was dissolved 83.1 g (0.5 mol) of p-cyclohexylphenol, and to the solution were added 150 g of 2-chloroethyl vinyl ether, 25 g of sodium hydroxide, 5 g of tetrabutylammonium bromide and 60 g of triethylamine, followed by reacting at 120° C. for 5 hours. The reaction solution was washed with water, and the excess 2-chloroethyl vinyl ether and toluene were distilled off. The oil thus obtained was purified by distillation under a reduced pressure to obtain 4-cyclohexylphenoxyethyl vinyl ether.

Workup

  1. washThe reaction solution was washed with water
  2. distillationthe excess 2-chloroethyl vinyl ether and toluene were distilled off
  3. customThe oil thus obtained
  4. distillationwas purified by distillation under a reduced pressure

Sources & evidence

ORD record
ord-e58ec32869fc4d9490fb8f12621ad5d1
Source dataset
uspto-grants-2011_12
Patent number
US08080362B2

Linked notes

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