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

HRID 6583

Reaction equation

HRID 6583 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 subsequently, 150 g of 2-chloroethyl vinyl ether, 25 g of sodium hydroxide, 5 g of tetrabutylammonium bromide and 60 g of triethylamine were added and reacted at 120° C. for 5 hours. The reaction solution was washed with water, excess chloroethyl vinyl ether and toluene were distilled off and the obtained oil was purified by distillation under reduced pressure to obtain 4-cyclohexylphenoxyethyl vinyl ether.

Workup

  1. customreacted at 120° C. for 5 hours
  2. washThe reaction solution was washed with water, excess chloroethyl vinyl ether and toluene
  3. distillationwere distilled off
  4. distillationthe obtained oil was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-2bff57c9dfc8421dbe6ed3b86c52a9d7
Source dataset
uspto-grants-2006_08
Patent number
US07083892B2

Linked notes

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