Hydrochloric Acid → 2-Chloro-1-(2,5-dimethylphenyl)ethan-1-one
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].Cl.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1>>[Cl:5][CH2:6][C:7]([C:17]1[CH:16]=[C:15]([CH3:18])[CH:14]=[CH:13][C:12]=1[CH3:11])=[O:8]Participants
Conditions
- Temperature
- 13.5 °C
Procedure
293.2 g [2.2 mol] of aluminum chloride are metered over the course of about 75 minutes into a mixture of 800 g p-xylene and 226 g [2 mol] of chloroacetyl chloride at 12-15° C. The reaction mixture is stirred at 12-15° C. for 2 hours, allowed to reach room temperature, stirred at room temperature for 30 minutes and then poured into 3000 ml of ice-water with 70 g of conc. hydrochloric acid. The cloudy organic phase is separated off, and the aqueous phase is extracted three times with 300 ml of ethyl acetate each time, and the combined organic phases are extracted twice with 200 ml of water each time and once with 100 ml of saturated aqueous NaCl solution. The organic phase is dried, evaporated and distilled as far as a bath temperature of 70° C./1 mbar. 363.6 g of yellowish oil result and, according to GC, contain 97.2% target product (96.8% of theory).
Workup
- customto reach room temperature
- stirringstirred at room temperature for 30 minutes
- customThe cloudy organic phase is separated off
- extractionthe aqueous phase is extracted three times with 300 ml of ethyl acetate each time
- extractionthe combined organic phases are extracted twice with 200 ml of water each time
- customThe organic phase is dried
- customevaporated
- distillationdistilled as far as a bath temperature of 70° C./1 mbar
- custom363.6 g of yellowish oil result
Sources & evidence
- ORD record
- ord-e49cee0936e64b38ba63d3a1d97a1a11
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629476B2
Reaction notes
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