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

HRID 1683143

Reaction equation

HRID 1683143 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 grams, 0.1 mole) and p-anisoyl chloride (17 grams, 0.1 mole) were dissolved in 200 milliliters of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 grams) 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 milliliters 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 milliliter portions of pentane, and dried, yielding 2,4,4'-trimethoxybenzophenone.

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 milliliter portions of pentane
  8. customdried

Sources & evidence

ORD record
ord-b789686693d84967a5e432cb57c5482c
Source dataset
uspto-grants-1997_06
Patent number
US05637262

Linked notes

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