Hydrochloric Acid → (2,4-Dimethoxyphenyl)(4-methoxyphenyl)methanone

HRID 10116

Reaction equation

HRID 10116 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[C:11](Cl)(=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][C:8]=1[C:11]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 90251,3-DimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 254174(2,4-Dimethoxyphenyl)(4-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Dimethoxybenzene (13.8 g) and p-anisoyl chloride (17 g) were dissolved in a reaction flask containing 200 mL of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 g) was added slowly to the reaction mixture over a period of 15 minutes with stirring. After stirring an additional 15 minutes, the contents of the flask were carefully poured into 200 mL of a mixture of ice and dilute hydrochloric acid. The organic fraction was separated and washed with water. The solvent was removed on a rotary evaporator leaving an oily product that solidified on standing. This solid was broken-up, washed with two 50 mL ortions of pentane, and dried, yielding (2,4-dimethoxy-phenyl)-(4-methoxy-phenyl)-methanone.

Workup

  1. stirringwith stirring
  2. stirringAfter stirring an additional 15 minutes
  3. customThe organic fraction was separated
  4. washwashed with water
  5. customThe solvent was removed on a rotary evaporator
  6. customleaving an oily product that
  7. washwashed with two 50 mL ortions of pentane
  8. customdried

Sources & evidence

ORD record
ord-37e898ff656e4c9e94b943275265965e
Source dataset
uspto-grants-2006_08
Patent number
US07094368B2

Linked notes

Loading…