2-Chloroethyl vinyl ether → [2-(Ethenyloxy)ethoxy]benzene

HRID 613451Notes

Reaction equation

HRID 613451 reaction equation
Cl[CH2:2][CH2:3][O:4][CH:5]=[CH2:6].[CH:7]1[CH:12]=[CH:11][C:10]([O-:13])=[CH:9][CH:8]=1.[Na+].C1(C2C(I=O)=C(S([O-])(=O)=O)C(C)=CC=2)C=CC=CC=1.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Na+]>ClCCl.Cl[Ti](Cl)(Cl)Cl.CC(CC)=O.C(O)(=O)C>[O:13]([CH2:6][CH2:5][O:4][CH:3]=[CH2:2])[C:10]1[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 4

HCID 80742-Chloroethyl vinyl etherHCID 4445035Phenolate SodiumHCID 11077530Sodium trifluoromethanesulfonimideHCID 86754987HCID 86754987, compound

Product 1

HCID 12437003[2-(Ethenyloxy)ethoxy]benzene

Reagents, catalysts & solvents 4

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The compound phenoxyethylvinylether is prepared by reacting chloroethylvinylether with sodium phenate, followed by polymerization in dichloromethane initiated with TiCl4 at -10° C. By reacting 8.2 g of the polymer with 9.8 g of phenyliodosotoluene sulfonate in 40 mL of a mixture of an equal volume of acetic acid and dichloromethane. A polyiodonium is obtained which is precipitated with ether. The ionic exchange reaction is carried similarly to that of example 3 between 12 g of polymer and 7 g of sodium bis(trifluoromethanesulfonyl)imide. After precipitation and washing with water, there is obtained a sticky mass which is used in a 50% solution of methylethylketone.

Workup

  1. customA polyiodonium is obtained which
  2. customis precipitated with ether
  3. customThe ionic exchange reaction
  4. customAfter precipitation
  5. washwashing with water
  6. customthere is obtained a sticky mass which

Sources & evidence

ORD record
ord-976dfdbd4e3545c19f9f87cbb4d04e15
Source dataset
uspto-grants-1999_12
Patent number
US06008267

Reaction notes

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