Anisole → 1,4-Bis(4-methoxyphenyl)butan-1-one

HRID 581111Notes

Reaction equation

HRID 581111 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:1](=[O:7])[CH2:2][CH2:3][CH2:4][C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 30181571,4-Bis(4-methoxyphenyl)butan-1-oneYield 226.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The crude acid chloride (2.07 g, 9.7 mmol) and anisole (1.26 g, 11.6 mmol) were dissolved in 1,2-dichloroethane (32 mL) and chilled in an ice bath. The mixture was treated with aluminum chloride (3.9 g, 29.1 mmol) in portions, stirred for 5 minutes, then mixed with ice water (50 mL). The mixture was extracted with dichloromethane (3×10 mL), and the extracts were combined, washed with saturated sodium chloride (100 mL), dried (MgSO4), then concentrated under reduced pressure. The residue was flushed through silica gel with 10:1 hexane/ethyl acetate then concentrated to give 1,4-bis-(4-methoxyphenyl)butan-1-one (2.49 g, 82%). 1H NMR (400 MHz, CDCl3): 7.90 (d, J=8.8 Hz, 2H), 7.11 (d, J=8.4 Hz, 2H), 6.91 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H), 3.86 (s, 3H), 3.78 (s, 3H), 2.90 (t, J=7.3 Hz, 2H), 2.65 (t, J=7.7 Hz, 2H), 2.02 (m, 2H) ppm. IR (NaCl): 1674, 1602, 1244 cm-1.

Workup

  1. temperaturechilled in an ice bath
  2. extractionThe mixture was extracted with dichloromethane (3×10 mL)
  3. washwashed with saturated sodium chloride (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was flushed through silica gel with 10:1 hexane/ethyl acetate
  7. concentrationthen concentrated

Sources & evidence

ORD record
ord-e8648ec1ffa94e2a91bba3fecbc1eb8a
Source dataset
uspto-grants-1999_07
Patent number
US05919768

Reaction notes

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