Acetyl chloride → 1-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]ethanone

HRID 2266141Notes

Reaction equation

HRID 2266141 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])([CH3:3])[CH3:2].[C:22](Cl)(=[O:24])[CH3:23].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[CH:1]([C:4]1[C:5]([S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:13])=[O:14])=[CH:6][C:7]([C:22](=[O:24])[CH3:23])=[C:8]([O:10][CH3:11])[CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 670535032-Isopropyl-4-methoxy-1-(toluene-4-sulfonyl)-benzene

Product 1

HCID 670534431-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]ethanoneYield 81.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a clear solution of 2-Isopropyl4-methoxy-1-(toluene-4-sulfonyl)-benzene (5.3 g, 16.56 mmol) in DCE (50 ml) was added acetyl chloride (2.0 g, 24.84 mmol) and AlCl3 (3.3 g, 24.84 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hrs and quenched by H2O (10 ml). Ten minutes after quenching, the aqueous solution was extracted into CH2Cl2. The combined extracts was washed with H2O, dried wover Na2SO4, filtered and concentrated. Flashed chromatography on silica gel (0 to 30% EtOAc in Hex) gave 1-[4-Isopropyl-2-methoxy-5-(toluene4-sulfonyl)-phenyl]-ethanone (4.7 g, 79%) as white solid.

Workup

  1. customquenched by H2O (10 ml)
  2. customTen minutes after quenching
  3. extractionthe aqueous solution was extracted into CH2Cl2
  4. washThe combined extracts was washed with H2O
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a601fd35eab04c98aa847269ac7905e5
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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