Water → 1-(4-Chlorophenyl)-2-propen-1-one

HRID 2402355Notes

Reaction equation

HRID 2402355 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].C(N(CC)CC)C.O.[Cl-].[Na+]>C(#N)C.C(OCC)(=O)C>[Cl:12][C:9]1[CH:8]=[CH:7][C:6]([C:4](=[O:5])[CH:3]=[CH2:2])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 775503,4'-Dichloropropiophenone

Product 1

HCID 109208881-(4-Chlorophenyl)-2-propen-1-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

60 g (295.5 mmol) of 3-chloro-1-(4-chlorophenyl)propan-1-one were dissolved in 900 ml of acetonitrile. With ice bath cooling, 41.2 ml (295.5 mmol) of triethylamine were then slowly added dropwise to the solution (exothermal reaction). After the addition had ended, the reaction solution was stirred at room temperature for 4 h. About one liter of water, one liter of ethyl acetate and about 250 ml of saturated sodium chloride solution were then added to the reaction mixture. The phases were separated, the organic phase was then dried over magnesium sulphate and filtered and the filtrate was concentrated to dryness. The crude product obtained was purified by chromatography on silica gel (about 1.3 kg) (mobile phase cyclohexane/ethyl acetate 6:1). This gave 45 g of the target product (91% of theory).

Workup

  1. temperatureWith ice bath cooling
  2. additionAfter the addition
  3. customThe phases were separated
  4. dry with materialthe organic phase was then dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-06a1c66cc40f43788d2083b462f99641
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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