Benzene → 6-Chloro-1-phenyl-1-hexanone

HRID 1758289Notes

Reaction equation

HRID 1758289 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12].[CH:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)(Cl)(Cl)Cl>[C:14]1([C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][Cl:5])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 880146-Chlorohexanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 41827306-Chloro-1-phenyl-1-hexanoneYield 34.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Aluminum chloride (16 g, 0.12 mol) is suspended in carbon tetrachloride (80 ml) and 6-chlorohexanoyl chloride (20 g, 0.12 mol) is added dropwise to the suspension with ice-cooling. After completion of addition, the mixture is stirred for 15 minutes and benzene (7.8 g, 0.1 mol) is added dropwise to the mixture with ice-cooling. After stirring with ice-cooling for 1 hour, the mixture is poured into ice-hydrochloric acid and extracted with carbon tetrachloride. The carbon tetrachloride extract is washed with water, saturated aqueous sodium bicarbonate, water and then saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The dried solution is distilled to obtain 5-chloropentyl phenyl ketone (7.3 g), b.p. 143°-150° C./0.5 mmHg.

Workup

  1. temperaturecooling
  2. additionAfter completion of addition
  3. temperaturecooling
  4. stirringAfter stirring with ice-
  5. temperaturecooling for 1 hour
  6. extractionextracted with carbon tetrachloride
  7. extractionThe carbon tetrachloride extract
  8. washis washed with water, saturated aqueous sodium bicarbonate, water
  9. dry with materialsaturated aqueous sodium chloride and dried over anhydrous magnesium sulfate
  10. distillationThe dried solution is distilled

Sources & evidence

ORD record
ord-ebdf040837c94c138e474efa3d66b450
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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