Benzoyl chloride → 3,4-Diethylbenzophenone

HRID 1276517Notes

Reaction equation

HRID 1276517 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[CH2:18][CH3:19])[CH3:11].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH2:10]([C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][C:17]=1[CH2:18][CH3:19])[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8])[CH3:11]

Participants

5

Procedure

A mixture of benzoyl chloride (1 eq) and 3,4-diethylbenzene (1.15 eq) was dissolved in 1,2-dichloroethane in a dry flask under argon and cooled in an ice bath with stirring. Aluminum chloride (1.3 eq) was added in portions to the reaction mixture at a rate to maintain the temperature below 10° C. Upon complete addition of the aluminum chloride, the ice bath was removed and the reaction mixture was stirred at room temperature for 18 h, then poured into cold water (100 mL) and extracted into ether (2×100 mL). The combined ether extracts were washed with water (25 mL), sodium bicarbonate solution (2×25 mL), water (25 mL), brine (25 mL), dried (MgSO4) and concentrated to provide the title compound as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureto maintain the temperature below 10° C
  3. customthe ice bath was removed
  4. stirringthe reaction mixture was stirred at room temperature for 18 h
  5. additionpoured into cold water (100 mL)
  6. extractionextracted into ether (2×100 mL)
  7. washThe combined ether extracts were washed with water (25 mL), sodium bicarbonate solution (2×25 mL), water (25 mL), brine (25 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-13992d8f48cb4fa5bed6e53ec46dbee0
Source dataset
uspto-grants-2000_12
Patent number
US06166072

Reaction notes

Loading…