4-Methylbenzoyl Chloride → 4-Methoxy-3,4'-dimethylbenzophenone

HRID 1076083Notes

Reaction equation

HRID 1076083 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][C:16]([C:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)=[O:8])=[CH:17][C:12]=1[CH3:11]

Participants

5

Reactant 3

HCID 134054-Methylbenzoyl ChlorideHCID 336372-MethylanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 142974374-Methoxy-3,4'-dimethylbenzophenone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

p-Toluoyl chloride (15.5g, 0.10 mole) is added dropwise at room temperature over a 1 hour period to a mixture of o-methylanisole (15.3 g, 0.125 mole) and aluminum chloride (AlCl3, 37.3g, 0.28 mole) in carbon disulfide (CS2, 50 ml) in a flask fitted with a stirrer, addition funnel, drying tube and reflux condenser. The reaction mixture is then refluxed for 1 hour, cooled and the carbon disulfide removed in vacuo. The residue is then slurried in methylene chloride and poured into 400 g of cracked ice containing 20 ml of concentrated hydrochloric acid. This mixture is then transferred to a separatory funnel and extracted with additional methylene chloride (3 × 15 ml) and the methylene chloride extract dried (anhydrous MgSO4) prior to concentrating in vacuo. The residue was then triturated with benzene. The benzene extract is then diluted with hexane which results in precipitation of 2.5 g. of product (10%), m.p. 73°-5°C.

Workup

  1. customfitted with a stirrer, addition funnel
  2. customdrying tube
  3. temperaturereflux condenser
  4. temperatureThe reaction mixture is then refluxed for 1 hour
  5. temperaturecooled
  6. customthe carbon disulfide removed in vacuo
  7. additionpoured into 400 g of cracked ice containing 20 ml of concentrated hydrochloric acid
  8. customThis mixture is then transferred to a separatory funnel
  9. extractionextracted with additional methylene chloride (3 × 15 ml)
  10. extractionthe methylene chloride extract
  11. dry with materialdried (anhydrous MgSO4)
  12. concentrationto concentrating in vacuo
  13. customThe residue was then triturated with benzene
  14. extractionThe benzene extract
  15. additionis then diluted with hexane which
  16. customresults in precipitation of 2.5 g

Sources & evidence

ORD record
ord-1f7118b11f4741379bb0a1127ab6abb9
Source dataset
uspto-grants-1976_05
Patent number
US03954875

Reaction notes

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