Hydrochloric Acid → 4-(m-Benzoylphenyl)-2-butanone

HRID 1731183Notes

Reaction equation

HRID 1731183 reaction equation
O=[C:2]([CH:18]([C:20](OCC)=O)C)[CH2:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].Cl.[OH2:26]>>[O:26]=[C:18]([CH3:20])[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 214956583-(2'-Oxo-3'-ethoxycarbonylbutyl)-benzophenone

Product 1

HCID 204960404-(m-Benzoylphenyl)-2-butanone

Conditions

Temperature
20 °C

Procedure

A mixture of 14.2 g of 3-(2'-oxo-3'-ethoxycarbonylbutyl)-benzophenone and 142 ml of 6N hydrochloric acid was refluxed with stirring of 17 hours and after cooling to 20° C, the mixture was diluted with 140 ml of water and extracted 3 times with 50 ml of methylene chloride. The organic phase was washed with 50 ml of an aqueous saturated sodium bicarbonate solution and twice with 50 ml of water, dried over sodium sulfate and evaporated to dryness under reduced pressure to obtain 10.76 g of 3-(3'-oxo-butyl)-benzophenone which was utilized as is for the next step.

Workup

  1. temperaturewas refluxed
  2. extractionextracted 3 times with 50 ml of methylene chloride
  3. washThe organic phase was washed with 50 ml of an aqueous saturated sodium bicarbonate solution and twice with 50 ml of water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8e71d8c5a2794fd488cb6d9959eabbf5
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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