Cumene → 4-Chloro-4'-isopropylbutyrophenone

HRID 1267687Notes

Reaction equation

HRID 1267687 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, 1.05 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-0c6d816fd1704efeaa6cfd422bbd48e4
Source dataset
uspto-grants-2003_04
Patent number
US06552200B2

Reaction notes

Loading…