Bis(2-chloroethyl) ether → HCID 12363404, compound

HRID 437684Notes

Reaction equation

HRID 437684 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[OH:12].[Cl:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18]Cl>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[O:12][CH2:18][CH2:17][O:16][CH2:15][CH2:14][Cl:13]

Participants

5

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 874592-Chloro-4-methoxyphenol

Product 1

HCID 12363404HCID 12363404, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 9.6 g. of 50% sodium hydride in 250 ml. of dry dimethylformamide was added in portions 31.6 g. of 2-chloro-4-methoxyphenol. To this mixture was added 143 g. of bis(2-chloroethyl) ether, and the reaction mixture was heated at reflux with stirring for 8 hours. The volatile solvent was removed, the residue partitioned between water and methylene dichloride, and the organic solution washed with water and dried over anhydrous magnesium sulfate. The product was twice distilled to give 2-[2-(2-chloro-4-methoxyphenoxy)ethoxy]ethyl chloride, b.p. 139°-140° C. (0.05 mm.).

Workup

  1. additionTo a suspension of 9.6 g
  2. additionTo this mixture was added 143 g
  3. temperatureat reflux
  4. customThe volatile solvent was removed
  5. customthe residue partitioned between water and methylene dichloride
  6. washthe organic solution washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe product was twice distilled

Sources & evidence

ORD record
ord-31caeff97ac0439185fde9fbe32f02b2
Source dataset
uspto-grants-1977_06
Patent number
US04031246

Reaction notes

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