2-Chloroethyl vinyl ether → HCID 53704608, compound

HRID 372822Notes

Reaction equation

HRID 372822 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH:5]=[CH2:6].[O:7]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>Cl.C(OCC)C>[Cl:1][CH2:2][CH2:3][O:4][CH:5]([O:20][C:17]1[CH:16]=[CH:15][C:14]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:19][CH:18]=1)[CH3:6]

Participants

5

Reactant 2

HCID 80742-Chloroethyl vinyl etherHCID 132544-Phenoxyphenol3×

Product 1

HCID 53704608HCID 53704608, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

64 g of freshly distilled 2-chloroethyl-vinyl ether is placed into a flask; one drop of concentrated hydrochloric acid is added, and thereupon an addition is made in portions at room temperature, with stirring, of 93 g of 4-phenoxy-phenol (duration of addition about 1 hour). During the addition of 4-phenoxy-phenol, the temperature rises to about 32°- 34° C, with the 4-phenoxy-phenol completely dissolving. After two further hours' stirring, the reaction mixture is diluted with 300 ml of diethyl ether; the ether solution is washed three times with 10% potassium hydroxide solution and three times with saturated sodium chloride solution. The ether solution is subsequently dried over sodium sulphate, and the ether and the readily volatile constituents (traces of 2-chloroethyl-vinyl ether) are completely removed in vacuo. There is obtained 1-(2-chloroethoxy)-1-[(4-phenoxy)-phenoxy]-ethane in the form of colorless oil having a refractive index of nD20 = 1.5516 (yield 98%).

Workup

  1. additionan addition
  2. customis made in portions at room temperature
  3. dissolutioncompletely dissolving
  4. washthe ether solution is washed three times with 10% potassium hydroxide solution and three times with saturated sodium chloride solution
  5. dry with materialThe ether solution is subsequently dried over sodium sulphate
  6. customthe ether and the readily volatile constituents (traces of 2-chloroethyl-vinyl ether) are completely removed in vacuo

Sources & evidence

ORD record
ord-4bada0933290425db5dc75d93656184c
Source dataset
uspto-grants-1978_05
Patent number
US04092365

Reaction notes

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