2-Chloroethanol → Benzhydryl 2-chloroethyl ether

HRID 652961Notes

Reaction equation

HRID 652961 reaction equation
[Cl:1][CH2:2][CH2:3][OH:4].S(=O)(=O)(O)O.[CH:10](O)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][O:4][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 1118Sulfuric AcidHCID 7037Benzhydrol

Product 1

HCID 141724Benzhydryl 2-chloroethyl etherYield 100.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 3.27 g of 2-chloroethanol in dry benzene (3.5 ml) was added 0.8 g of conc. sulfuric acid and the mixture was heated, under argon atmosphere, at 50° C. To the mixture was added slowly a solution of 5.0 g of benzhydrol in dry benzene (6.5 ml) and, after 30 minutes from the addition, the whole mixture was refluxed for 1.5 hours. After the mixture was allowed to cool, the benzene layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, to give 6.7 g of benzhydryl 2-chloroethyl ether.

Workup

  1. additionafter 30 minutes from the addition
  2. temperaturethe whole mixture was refluxed for 1.5 hours
  3. temperatureto cool
  4. washthe benzene layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-de20cc6f8a87461ca0fe015b58495983
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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