Anisole → (4-Ethylphenyl)(4-methoxyphenyl)methanone

HRID 1713575Notes

Reaction equation

HRID 1713575 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)[CH3:2].[C:12]1([O:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([C:15]2[CH:16]=[CH:17][C:12]([O:18][CH3:19])=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 853684-Ethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12343547(4-Ethylphenyl)(4-methoxyphenyl)methanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-ethylbenzoyl chloride (8.6 g, 51.0 mmol) in anhydrous DCM (200 mL) at −5 to 0° C., was added anisole (5.46 g, 50.5 mmol), followed by addition of aluminum chloride (7.0 g, 52.5 mmol) over 5 minutes. The resulting yellow reaction mixture was stirred at 0° C. for 1 h and then at rt for 2 h. The reaction mixture was poured into ice water (300 mL), extracted with DCM (300 mL×2). Combined DCM solution was washed with 1M aqueous HCl (300 mL×1), 2 N aqueous NaOH (200 ml×1), brine (400 mL×2), dried over MgSO4 and evaporated to give the product, 12.2 g, yield 100%. 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=8.7 Hz, 2H), 7.68 (d, J=8.1 Hz, 2H), 7.27 (d, J=8.1 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 3.87 (s, 3H), 2.71 (q, J=7.5 Hz, 2H), 1.28 (t, J=7.5 Hz, 3H). ESI-MS m/z 240.9 (M+H)+.

Workup

  1. waitat rt for 2 h
  2. extractionextracted with DCM (300 mL×2)
  3. washCombined DCM solution was washed with 1M aqueous HCl (300 mL×1), 2 N aqueous NaOH (200 ml×1), brine (400 mL×2)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give the product, 12.2 g, yield 100%

Sources & evidence

ORD record
ord-4eb310d55fa6491fabc2ba3dec1cc831
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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