Anisole → (4-Methoxyphenyl)(4-methylphenyl)methanone

HRID 1525310Notes

Reaction equation

HRID 1525310 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]1([O:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:18][O:17][C:11]1[CH:16]=[CH:15][C:14]([C:6]([C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=2)=[O:7])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 134054-Methylbenzoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 32113(4-Methoxyphenyl)(4-methylphenyl)methanoneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methylbenzoyl chloride, 32-a, (10 g, 65 mmol) and anisole (8.8 g, 81 mmol) in DCM anhydrous was added aluminum(III) chloride (10.8 g, 81 mmol), the reaction mixture was then stirred for 10 h at ambient temperature. The resulting mixture was concentrated under reduce pressure, 100 ml of water was added, filtered, the residue was dried in vacuo. The product was obtained as a white solid, 32-b, (14 g, 95% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.25 (s, 3H), 3.71 (s, 3H), 6.85-6.89 (m, 2H), 7.11-7.19 (m, 6H). LC-MS 227 [MH]+.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additionwas added
  3. filtrationfiltered
  4. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-a5ede40872dd4f24951a52faa9c269ce
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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