Thionyl Chloride → Benzene, (2-chloroethoxy)-

HRID 2371581Notes

Reaction equation

HRID 2371581 reaction equation
[O:1]([CH2:8][CH2:9]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl>[O:1]([CH2:8][CH2:9][Cl:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 31236Phenoxyethanol

Product 1

HCID 12156Benzene, (2-chloroethoxy)-Yield 101.7%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a three-necked flask fitted with a stirrer, dropping funnel, thermometer and reflux condenser, was added 34.7 g 2-phenoxy-ethanol, 75 g dichloromethane and 1.25 g benzyl-trimethyl-ammonium chloride. The mixture was cooled to about 0° C. and 34 g thionyl chloride was added dropwise over a period of 45 minutes. After this addition, the mixture was warmed to room temperature, stirred for an hour and then heated to reflux (50° C.) for an additional three hours. At the end of the reaction (determined by GLC) the mixture was washed with water, an aqueous 10% sodium hydroxide solution and then again with water. The solvent was distilled off to afford 40 g of 2-phenoxy-ethyl chloride in a concentration of 95%.

Workup

  1. customInto a three-necked flask fitted with a stirrer
  2. temperaturethermometer and reflux condenser
  3. additionAfter this addition
  4. temperaturethe mixture was warmed to room temperature
  5. temperatureheated
  6. temperatureto reflux (50° C.) for an additional three hours
  7. customAt the end of the reaction (determined by GLC) the mixture
  8. washwas washed with water
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-dc99c14dd9a54b7da6d169b3323e467b
Source dataset
uspto-grants-1992_03
Patent number
US05093526

Reaction notes

Loading…