Toluene → 4-Chloro-4'-methylbutyrophenone

HRID 1857838Notes

Reaction equation

HRID 1857838 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:15]1[CH:16]=[CH:17][C:12]([CH3:18])=[CH:13][CH:14]=1)=[O:10]

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 987454-Chloro-4'-methylbutyrophenoneYield 95%

Conditions

Temperature
3 °C

Procedure

Suspend anhydrous AlCl3 (156 g, 1.15 mol) in toluene (1500 mL) and cool to 2-4° C. Add, by slow addition, a solution of 4-chlorobutyryl chloride (165.5 g, 1.15 mol) in toluene (300 mL). Stir for 15 minutes and pour into stirring ice-water (2.5 L). Stir for 30 hours, decant the toluene and extract the aqueous phase with toluene (700 mL). Combine the organic layers and wash three times with water (1 L, 1 L, 500 mL). Evaporate the solvent in vacuo to give the title compound as a pale yellow oil (292.3 g, 95%).

Workup

  1. additionAdd, by slow addition
  2. additionpour
  3. stirringStir for 30 hours
  4. customdecant the toluene
  5. extractionextract the aqueous phase with toluene (700 mL)
  6. washCombine the organic layers and wash three times with water (1 L, 1 L, 500 mL)
  7. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-91025e41b2744a4ab6dfe272d16cd9bc
Source dataset
uspto-grants-2000_11
Patent number
US06147216

Reaction notes

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