Hydrochloric Acid → 4-Chloro-3'-nitrobenzophenone

HRID 614698Notes

Reaction equation

HRID 614698 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=[O:12])([O-:7])=[O:6].Cl>ClC1C=CC=CC=1>[Cl:1][C:8]1[CH:9]=[CH:10][C:14]([C:11](=[O:12])[C:10]2[CH:14]=[CH:15][CH:16]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8495Benzoyl chloride, 3-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 7673464-Chloro-3'-nitrobenzophenoneYield 147.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

30.5 g (0.27 mol) of chlorobenzene and 36 g (0.27 mol) of aluminium chloride are introduced into a 250 cm3 flask and 25 g (0.135 mol) of m-nitrobenzoyl chloride dissolved in 15 cm3 of chlorobenzene are added dropwise. The mixture is heated for 5 hours at between 50° and 60° C. and is then allowed to cool and is hydrolysed with 500 g of ice + 20 cm3 of concentrated HCl (d = 1.18); the batch is extracted with ether and the extract is washed with aqueous sodium hydroxide solution (strength 30 g/l) and then with water; the ether phase is dried, decolorised and then evaporated in vacuo; 26 g of the expected ketone are obtained. Melting point 97° C.

Workup

  1. additionare added dropwise
  2. temperatureThe mixture is heated for 5 hours at between 50° and 60° C.
  3. temperatureto cool
  4. extractionthe batch is extracted with ether
  5. washthe extract is washed with aqueous sodium hydroxide solution (strength 30 g/l)
  6. dry with materialthe ether phase is dried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d8b55bf5281f436683cd25c2d2939e1e
Source dataset
uspto-grants-1979_03
Patent number
US04146385

Reaction notes

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