Anisole → Desoxyanisoin

HRID 1405333Notes

Reaction equation

HRID 1405333 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.[C:13]1([O:19][CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Al+3].[Cl-].[Cl-].[Cl-]>S(Cl)(Cl)=O.ClCCl.O>[CH3:20][O:19][C:13]1[CH:18]=[CH:17][C:16]([C:10](=[O:12])[CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 7519AnisoleHCID 76904-Methoxyphenylacetic AcidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67120DesoxyanisoinYield 84.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-(4-methoxyphenyl)acetic acid (5.0 g, 30.12 mmol) in thionyl chloride (50 mL) was stirred for 3 hr at reflux and then concentrated in vacuo to give a residue, which was dissolved in dichloromethane (10 mL) and then added dropwise to a solution of anisole (6.51 g, 60.28 mmol) and AlCl3 (11.97 g, 90.00 mmol) in dichloromethane (120 mL). The resulting solution was stirred for 3 h at room temperature, then diluted with water (100 mL), extracted with dichloromethane (3×80 mL), dried over magnesium sulfate, and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with (1%˜2% ethyl acetate in petroleum ether) to afford 1,2-bis(4-methoxyphenyl)ethanone as a white solid (6.5 g, 84%).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated in vacuo
  3. customto give a residue, which
  4. extractionextracted with dichloromethane (3×80 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a residue, which
  8. customwas purified by silica gel column chromatography with (1%˜2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-ab759286c6de46e39880c53d3a4b97a3
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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