Sulfuric Acid → 3-Chloro-1-(3,4-diethylphenyl)propan-1-one

HRID 577620Notes

Reaction equation

HRID 577620 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH3:10])[CH3:2].[C:11](Cl)(=[O:14])[CH2:12][CH3:13].[Al+3].[Cl-:17].[Cl-].[Cl-].S(=O)(=O)(O)O>[N+](C)([O-])=O>[Cl:17][CH2:13][CH2:12][C:11]([C:7]1[CH:6]=[CH:5][C:4]([CH2:9][CH3:10])=[C:3]([CH2:1][CH3:2])[CH:8]=1)=[O:14]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 86571,2-DiethylbenzeneHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 222383023-Chloro-1-(3,4-diethylphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

1,2-Diethylbenzene (10.9 g, 74.6 mmol) and propionyl chloride (9.7 g, 74.6 mmol) are added dropwise to AlCl3 (22.3 g, 167.8 mmol) in nitromethane (75 mL) over 30 min. The reaction mixture is stirred at room temperature for 2 hours, after which 70 g of ice and 14 mL concentrated sulphuric acid are added. The aqueous phase is extracted with ether, and the combined organic phases extracted with 2N HCl and saturated aqueous NaCl. The organic phase is further treated with activated charcoal, magnesium sulphate, and filtered, and the solvent removed in vacuo.

Workup

  1. extractionThe aqueous phase is extracted with ether
  2. extractionthe combined organic phases extracted with 2N HCl and saturated aqueous NaCl
  3. additionThe organic phase is further treated with activated charcoal, magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-201b88bf6fc740fa8390e2decb1b2841
Source dataset
uspto-grants-2015_05
Patent number
US09040559B2

Reaction notes

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