Hydrochloric Acid → HCID 22027811, compound

HRID 1791130Notes

Reaction equation

HRID 1791130 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Cl:10][CH2:11][C:12](Cl)=[O:13].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[Cl:10][CH:11]([C:5]1[CH:4]=[C:3]([CH3:9])[C:2]([Cl:1])=[CH:7][C:6]=1[CH3:8])[C:12]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 32883Chloro-p-xyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22027811HCID 22027811, compoundYield 134.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-chloro-1,4-dimethyl-benzene (5 g, 35.56 mmol) and chloroacetylchloride (4.0 g, 35.6 mmol) was cooled to 0° C. and treated with aluminum chloride (4.74 g, 35.6 mmol) in small portions. The reaction slurry was diluted with dichloromethane and allowed to warm to room temperature. After 30 min the reaction was poured onto a mixture of ice and 10 mL of concentrated aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate and the organic layers were combined and washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried (Na2SO4) and concentrated to give approximately 7 g of pure product as a white powder.

Workup

  1. temperatureto warm to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a1c68688fb7b47d79881ac9a39a8a64e
Source dataset
uspto-grants-2006_07
Patent number
US07074783B2

Reaction notes

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