Anisole → (4-Methoxyphenyl)(3-nitrophenyl)methanone

HRID 2103118Notes

Reaction equation

HRID 2103118 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3].[N+:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20])([O-:15])=[O:14]>ClCCCl>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:19]([C:18]2[CH:22]=[CH:23][CH:24]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=2)=[O:20])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 8495Benzoyl chloride, 3-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 794540(4-Methoxyphenyl)(3-nitrophenyl)methanoneYield 84.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a cold (0° C.) mixture of anisole (17.7 mL, 0.162 mol, 1.0 eq.) and aluminium trichloride (26.9 g, 0.202 mol, 1.25 eq.) in 1,2-dichloroethane (140 mL) was slowly added 3-nitrobenzoylchloride (30 g, 0.162 mol). The cooling bath was removed, and the reaction mixture was stirred 2 h at 20° C. The reaction mixture was poured into ice water. Concentrated hydrochloric acid (5 mL) was added. The aqueous layer was extracted with dichloromethane (2 times). The combined organic layers were dried over sodium sulfate, filtered and the volatiles were removed in vacuo. Purification by flash chromatography afforded the title compound (35.1 g, 84%) as an orange solid, m.p.: 88-89° C.

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction mixture was poured into ice water
  3. additionConcentrated hydrochloric acid (5 mL) was added
  4. extractionThe aqueous layer was extracted with dichloromethane (2 times)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customthe volatiles were removed in vacuo
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-ed1864c5dd0446028ae2fe19893df6ab
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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