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

HRID 2212796Notes

Reaction equation

HRID 2212796 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 mole) of p-cyclohexylphenol. Thereto, 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 underwent reaction at 120° C. for 5 hours. The resulting reaction solution was washed with water, and therefrom the excess chloroethyl vinyl ether and toluene were distilled away. The oil thus obtained was purified by reduced-pressure distillation to yield 4-cyclohexylphenoxyethyl vinyl ether.

Workup

  1. customunderwent reaction at 120° C. for 5 hours
  2. customThe resulting reaction solution
  3. washwas washed with water
  4. distillationthe excess chloroethyl vinyl ether and toluene were distilled away
  5. customThe oil thus obtained
  6. distillationwas purified by reduced-pressure distillation

Sources & evidence

ORD record
ord-f44b8b8401e44c3eab6c874307cc1255
Source dataset
uspto-grants-2006_09
Patent number
US07105273B2

Reaction notes

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