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

HRID 2351857Notes

Reaction equation

HRID 2351857 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 9.8 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. Anal., Calcd. for C15H13NO4 : C, 66.41; H, 4.83; N, 5.16.5. Found: C, 66.33; H, 4.95; N, 4.98.

Workup

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

Sources & evidence

ORD record
ord-1a2ad6a27d134cddadbc71c9d06f51ef
Source dataset
uspto-grants-1989_10
Patent number
US04874761

Reaction notes

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