Water → (4-Methoxyphenyl)(2-methyl-3-nitrophenyl)methanone

HRID 1904907Notes

Reaction equation

HRID 1904907 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[C:18]1([O:24][CH3:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(Cl)Cl>[CH3:25][O:24][C:18]1[CH:23]=[CH:22][C:21]([C:8]([C:7]2[C:6]([CH3:5])=[C:14]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 121948722-Methyl-3-nitrobenzoyl chloride

Product 1

HCID 14535915(4-Methoxyphenyl)(2-methyl-3-nitrophenyl)methanoneYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 95.6 g (0.716 mole) of aluminum chloride in 500 ml of methylene dichloride was added, rapidly and with stirring, a solution of 110.1 g (0.551 mole) of 2-methyl-3-nitrobenzoyl chloride in 400 ml of methylene dichloride. The mixture was then transferred to an addition funnel, added with stirring to a solution of 59.8 g (0.551 mole) of anisole over a thirty minute period, and the reaction mixture then heated under reflux for two hours. The mixture was decomposed by the careful addition, with stirring, of 1 liter of water and then filtered. The organic layer was separated from the aqueous layer, dried and taken to dryness, and the residue recrystallized from ethyl acetate to give 102.9 g of 3-(4-methoxybenzoyl)-2-methylnitrobenzene, m.p. 110°-113° C.

Workup

  1. additionwas added
  2. customThe mixture was then transferred to an addition funnel
  3. additionadded
  4. temperaturethe reaction mixture then heated
  5. temperatureunder reflux for two hours
  6. additionThe mixture was decomposed by the careful addition
  7. filtrationfiltered
  8. customThe organic layer was separated from the aqueous layer
  9. customdried
  10. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-abd7a68ba31548adbc60b9e827a60b9e
Source dataset
uspto-grants-1989_06
Patent number
US04840950

Reaction notes

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