Thionyl Chloride → 2-(4-Chlorophenyl)ethyl chloride

HRID 1848692Notes

Reaction equation

HRID 1848692 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>CN(C)C(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][Cl:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 74647p-Chlorophenethylic alcohol

Product 1

HCID 37903592-(4-Chlorophenyl)ethyl chlorideYield 105.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideCatalyst

Conditions

Temperature
55 °C

Procedure

In a 250-mL round bottom flask equipped with overhead stirring, a thermocouple, a condenser, and a nitrogen bubbler vented to a caustic scrubber, 2-(4-chlorophenyl)ethanol (40.011 g, 255 mmol) and N,N-dimethylacetamide (1.197 mL, 12.77 mmol) were heated to 55° C. Thionyl chloride (19.58 mL, 268 mmol) was added slowly and significant off-gassing was observed. After the addition was complete the resulting dark-brown solution was stirred at between 60 and 64° C. for 1.5 hours and then allowed to cool to room temperature and stirred overnight to give the title compound as a dark-brown oil (47.060 g, including DMA and thionyl chloride).

Workup

  1. customIn a 250-mL round bottom flask equipped with overhead stirring
  2. additionAfter the addition
  3. temperatureto cool to room temperature
  4. stirringstirred overnight

Sources & evidence

ORD record
ord-83ba028f48194462ba3cce07620353d6
Source dataset
uspto-grants-2015_02
Patent number
US08952197B2

Reaction notes

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