4-Chlorobenzotrichloride → 3,4-Dichlorophenyltrichloromethane

HRID 622267

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([Cl:11])([Cl:10])[Cl:9])=[CH:4][CH:3]=1.[Cl:12]Cl>Cl>[Cl:12][C:7]1[CH:6]=[C:5]([C:8]([Cl:9])([Cl:10])[Cl:11])[CH:4]=[CH:3][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 70 °C

Procedure

In this apparatus, a mixture of 1,725 g (7.5 moles) of 4-chlorobenzotrichloride and 12 g (0.075 mole) of FeCl3 was heated to 70° C. and circulated. The introduction of 585 g (8.25 moles) of chlorine gas was then started. (chlorine gas was fed in at a rate such that no chlorine was detectable in the exit gas.) The reaction was complete after 5 hours. 2 liters of dilute hydrochloric acid were added to the reaction mixture and the organic phase was separated off, washed twice with 2 liters of water and dried over CaCl2. Subsequent fractional distillation gave 1,824 g of 3,4-dichlorobenzotrichloride (92% of theory) (98% purity according to a gas chromatogram), of boiling point 138°-140° C. at 12 mbar.

Workup

customthe organic phase was separated off
washwashed twice with 2 liters of water
dry with materialdried over CaCl2
distillationSubsequent fractional distillation

Sources & evidence

ORD record: ord-7b5fe7f8da4e4d218aa780c77a7ecd7d
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04769503

Linked notes

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