3-Chloro-1-(3,4-diethylphenyl)propan-1-one → HCID 22238300, compound

HRID 2401580Notes

Reaction equation

HRID 2401580 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH3:13])=[C:8]([CH2:14][CH3:15])[CH:7]=1)=[O:5]>S(=O)(=O)(O)O>[CH2:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[CH2:14][CH3:15])[C:4](=[O:5])[CH2:3][CH2:2]2)[CH3:13]

Participants

3

Reactant 1

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

Product 1

HCID 22238300HCID 22238300, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

3-chloro-1-(3,4-diethylphenyl)-1-propanone (15.5 g) is dissolved in 66 mL concentrated sulphuric acid and heated to 90° C. for 4 hours. The reaction mixture is cooled, ice (70 g) is added, and the aqueous solution extracted twice with toluene. The organic layer is washed with sodium bicarbonate, saturated aqueous NaCl, and treated with activated charcoal and magnesium suphate. After filtration, the solvent is removed in vacuo. The product is purified by flash column chromatography (silica, hexane/ethylacetate 10:1), and further crystallised in hexane.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionthe aqueous solution extracted twice with toluene
  3. washThe organic layer is washed with sodium bicarbonate, saturated aqueous NaCl
  4. additiontreated with activated charcoal and magnesium suphate
  5. filtrationAfter filtration
  6. customthe solvent is removed in vacuo
  7. customThe product is purified by flash column chromatography (silica, hexane/ethylacetate 10:1)
  8. customfurther crystallised in hexane

Sources & evidence

ORD record
ord-8750224863e04deebb15eea90721e107
Source dataset
uspto-grants-2014_08
Patent number
US08796307B2

Reaction notes

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