1,2-Dichloroethane → 1-(2-Chloroethoxy)-2-methoxybenzene

HRID 408447Notes

Reaction equation

HRID 408447 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[Cl:10][CH2:11][CH2:12]Cl.[OH-].[K+]>>[Cl:10][CH2:11][CH2:12][O:3][C:2]1[CH:4]=[CH:5][CH:6]=[CH:7][C:1]=1[O:8][CH3:9]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 460GuaiacolHCID 14797Potassium Hydroxide

Product 1

HCID 41438391-(2-Chloroethoxy)-2-methoxybenzeneYield 52.2%

Procedure

A mixture of 52.88 g (0.426 mol) of guaiacol (34), 50 ml (0.426 mol) of 1,2-dichloroethane, 88.3 g (0.639 mol) of potassium hydroxide and heated at reflux for 24 h. The mixture was concentrated and extracted into ethyl acetate and evaporate the solvent and purified by column chromatography to gave 41.47 g (52%) of 1-(2-Chloroethoxy)-2-methoxy benzene (35) as a white solid, mp 42-43° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted into ethyl acetate
  5. customevaporate the solvent
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-72714eaec11348fbae0f4db08e1f8e44
Source dataset
uspto-grants-2014_06
Patent number
US08759339B2

Reaction notes

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