Cumene → 4-Chloro-4'-isopropylbutyrophenone

HRID 1836759Notes

Reaction equation

HRID 1836759 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[C:12]1([CH:18]([CH3:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:15]1[CH:16]=[CH:17][C:12]([CH:18]([CH3:20])[CH3:19])=[CH:13][CH:14]=1)=[O:10]

Participants

5

Reactant 3

HCID 7406CumeneHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 987444-Chloro-4'-isopropylbutyrophenoneYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
6.5 °C

Procedure

Slurry aluminum chloride (140.9 g, 1.075 mol) and 4-chlorobutyryl chloride (148 g, 1.5 mol) in methylene chloride (1.0L) add, by dropwise addition, cumene (125 g, 1.04 mol) over a thirty minute period under a nitrogen atmosphere while maintaining the internal temperature between 5-8° C. with an ice bath. Allow the stirred solution to come to room temperature and continue stirring under nitrogen for 14 hours. Cautiously add the methylene chloride solution to 1L of crushed ice with stirring and add additional methylene chloride (400 mL). Separate the organic phase and wash with 10% hydrochloric acid (3×300 mL), water (3×300 mL), 10% sodium bicarbonate (3×300 mL) and water (3×300 mL). Dry (MgSO4), filter and wash with methylene chloride (150 mL). Evaporate the solvent to give the title compound (203 g, 86%) as a clear oil which crystallizes on standing; mp 35-37° C.

Workup

  1. customto come to room temperature
  2. stirringwith stirring
  3. customSeparate the organic phase
  4. washwash with 10% hydrochloric acid (3×300 mL), water (3×300 mL), 10% sodium bicarbonate (3×300 mL) and water (3×300 mL)
  5. dry with materialDry (MgSO4)
  6. filtrationfilter
  7. washwash with methylene chloride (150 mL)
  8. customEvaporate the solvent

Sources & evidence

ORD record
ord-a103044f56e44f10a5334e906f1c51e3
Source dataset
uspto-grants-2004_08
Patent number
US06777555B2

Reaction notes

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