Hydrochloric Acid → 1-Chloro-2-(1-chloroethyl)benzene

HRID 60530Notes

Reaction equation

HRID 60530 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12](O)[CH3:13].[ClH:15]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([Cl:15])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 260821-(2-Chlorophenyl)ethanol

Product 1

HCID 5870341-Chloro-2-(1-chloroethyl)benzeneYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (1.49 g, 12.6 mmol) was added to 1-(2-chlorophenyl)ethanol (1.0 g, 6.3 mmol) in toluene (50 mL) and the mixture was allowed to stir at room temperature for 2 h. To the reaction mixture was added 10% aq. HCl solution (20 mL). The organic phase was separated and washed with another portion of 10% aq. HCl solution, brine (20 mL) and then separated, dried and evaporated to provide 1-chloro-2-(1-chloroethyl)benzene in 72% yield.

Workup

  1. customThe organic phase was separated
  2. washwashed with another portion of 10% aq. HCl solution, brine (20 mL)
  3. customseparated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-2ae666cdc1f14021a45edc0c84686863
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Reaction notes

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