Hydrochloric Acid → 1,4-Bis(4-chlorophenyl)-2-butene-1,4-dione

HRID 66047

Reaction equation

HRID 66047 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-:8].[Al+3].[Cl-].[Cl-].[C:12](Cl)(=[O:18])/[CH:13]=[CH:14]/[C:15](Cl)=[O:16].Cl>C(=S)=S>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]([CH:13]=[CH:14][C:15](=[O:16])[C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=2)=[O:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7964ChlorobenzeneHCID 5325504Fumaryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2320011,4-Bis(4-chlorophenyl)-2-butene-1,4-dione

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Chlorobenzene (0.4 mol) and aluminium chloride (0.5 mol) in carbon disulphide (30 ml) were stirred at 50°-60°. Fumaryl chloride (0.2 mol) was added dropwise at a brisk rate over 30 minutes and refluxing was continued for a further 15 minutes. The residue was poured into crushed ice (1 kg) and concentrated hydrochloric acid (15.0 ml). The semi-solid was filtered off, washed with ether and ethanol, and recrystallised from ethyl acetate/ethanol to give pale yellow needles of di-(p-chlorobenzoyl) ethylene m.p. 175°-176°. Analysis:

Workup

  1. temperaturerefluxing
  2. additionThe residue was poured
  3. filtrationThe semi-solid was filtered off
  4. washwashed with ether and ethanol
  5. customrecrystallised from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-7268eb315e164f72ba51cc9181c1bd1a
Source dataset
uspto-grants-1978_12
Patent number
US04130409

Linked notes

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