Water → 3,4-Diethylbenzophenone

HRID 583471

Reaction equation

HRID 583471 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH3:10])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[CH2:9][CH3:10])[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:22])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 86571,2-DiethylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 215845983,4-DiethylbenzophenoneYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred ice bath cooled solution of diethylbenzene (1.7 mL, 10 mmol) in methylene chloride (30 mL) under nitrogen was added aluminum chloride (2.93 g, 22 mmol). A slight exotherm resulted. To the resulting reaction mixture was added benzoyl chloride (1.2 mL, 10 mmol). The reaction mixture was allowed to warm to room temperature and was then stirred at room temperature for 1.5 hours. The reaction mixture was poured into 60 mL of iced water and stirred for 20 minutes. The resulting mixture was extracted with methylene chloride (2×40 mL). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to afford the crude product as an orange oil. The crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/hexane) to afford 1.22 g (51%) of the product as a yellow oil: 1H NMR (CDCl3) δ 7.85-7.41 (m, 7H), 7.30-7.20 (m, 1H) 2.83-2.61 (m, 4H), 1.35-1.17 (m, 6H); 13C NMR (CDCl3) δ 196.8, 147.0, 141.9, 138.1, 135.3, 132.1, 132.1, 130.1, 130.0, 128.1, 128.1, 25.6, 25.4, 15.1, 15.0; Anal. Calcd for C17H18O. Theoretical: C, 85.67; H, 7.61. Found: C, 85.38; H, 7.42.

Workup

  1. customA slight exotherm resulted
  2. customTo the resulting reaction mixture
  3. stirringstirred for 20 minutes
  4. extractionThe resulting mixture was extracted with methylene chloride (2×40 mL)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product as an orange oil
  8. customThe crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-56bd2c972cc34b548f350f35ca3c6715
Source dataset
uspto-grants-1999_07
Patent number
US05929117

Linked notes

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