1,4-Dichlorobenzene → Ethanone, 1-(2,5-dichlorophenyl)-

HRID 49695

Reaction equation

[CH:1]1[C:6]([Cl:7])=[CH:5][CH:4]=[C:3]([Cl:8])[CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:13](Cl)(=[O:15])[CH3:14]>O>[CH3:14][C:13]([C:4]1[CH:5]=[C:6]([Cl:7])[CH:1]=[CH:2][C:3]=1[Cl:8])=[O:15]

Participants

Conditions

Temperature: 110 °C

Procedure

147 g (1.0 mol) of p-dichlorobenzene are completely melted at 60° C. in an apparatus having an attached dropping funnel, stirrer and reflux condenser. 120 g (0.9 mol) of anhydrous AlCl3 are added to the melt. 39.3 g (0.5 mol) of acetyl chloride are then added dropwise to the readily stirrable suspension at 60° C. in the course of about 1 hour, a clear solution slowly resulting. After heating to 110° C., the mixture is stirred at this temperature for 7 hours. After cooling to room temperature, the brown reaction mass is hydrolysed by cautious decantation onto a mixture of 200 ml of water and 200 g of ice. The temperature of the mixture is kept between 30 and 40° C. during the hydrolysis by external cooling. After separation of the phases, the lower, organic phase is washed with 400 ml of water and, after fresh phase separation, subjected to fractional distillation. The aqueous phases are discarded.

Workup

temperaturereflux condenser
customa clear solution slowly resulting
temperatureAfter cooling to room temperature
customThe temperature of the mixture is kept between 30 and 40° C. during the hydrolysis by external cooling
customAfter separation of the phases
washthe lower, organic phase is washed with 400 ml of water
customafter fresh phase separation
distillationsubjected to fractional distillation

Sources & evidence

ORD record: ord-cc52007598bd47f7bf8ccc17a00f4812
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706930B2

Linked notes

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