Anisole → 3-CYANO-4'-METHOXYBENZOPHENONE

HRID 1721915Notes

Reaction equation

HRID 1721915 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[N:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:16]1([O:22][CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([C:19]1[CH:20]=[CH:21][C:16]([O:22][CH3:23])=[CH:17][CH:18]=1)=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 3084833-Cyanobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 122893893-CYANO-4'-METHOXYBENZOPHENONE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, 16.5 g. of 3-cyanobenzoyl chloride were added to 80 ml. of methylene chloride. The temperature was brought to approximately 0° C. by means of an external ice bath and kept cold while 20 g. of aluminum chloride were added in portions. A solution of 10.8 g. of anisole in 20 ml. of methylene chloride were added to the reaction solution. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was poured into a mixture of ice water/hydrochloric acid and extracted with ethyl acetate. The layers were separated and the organic layer was washed with water, dried, and concentrated in vacuo. The residue was crystallized from toluene/hexane to which a small amount ethyl acetate had been added to provide 7.7 g. of the desired subtitle intermediate, m.p. 85°-88° C.

Workup

  1. customThe temperature was brought to approximately 0° C. by means of an external ice bath
  2. extractionextracted with ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from toluene/hexane to which a small amount ethyl acetate
  8. additionhad been added
  9. customto provide 7.7 g

Sources & evidence

ORD record
ord-7749db9538a04fa19b9cb2006ec69267
Source dataset
uspto-grants-1989_08
Patent number
US04853398

Reaction notes

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