Anisole → HCID 13427164, compound

HRID 2372365Notes

Reaction equation

HRID 2372365 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](Cl)=[O:8].[C:10]1([O:16][CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:17][O:16][C:10]1[CH:15]=[CH:14][C:13]([C:7](=[O:8])[CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 1623622-Thiopheneacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13427164HCID 13427164, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Thiophenylacetyl chloride (12.38 g, 77.1 mmol) in CH2Cl2 (40 ml) was added to a solution of anisole (8.33 g, 77.1 mmol) and AlCl3 (10.3 g, 77.1 mmol) in CH2Cl2 (200 ml) at room temperature. The reaction was completed after 2 hours, and the mixture was poured over a 10% HCl/ice slurry. The organic layer was washed with H2O and brine, dried over MgSO4, and the solvent was removed under reduced pressure. The crude solid was chromatographed on SiO2 (1 kg) eluting with CH2Cl2 /Hexane, 3/1, to afford 23 (9.37 g, 52.4%), m.p. 44.0°-45.5° C. and the ortho isomer (2.14 g, 12%)

Workup

  1. washThe organic layer was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customThe crude solid was chromatographed on SiO2 (1 kg)
  5. washeluting with CH2Cl2 /Hexane, 3/1

Sources & evidence

ORD record
ord-d1d1cca65a2c4bc49ddadea4e5a757ef
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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