Benzoyl chloride → HCID 18702002, compound

HRID 2289109Notes

Reaction equation

HRID 2289109 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][CH3:13].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:10][O:9][C:6]1[CH:5]=[C:4]([CH2:11][CH2:12][CH3:13])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:21]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12262497HCID 12262497, compound

Product 1

HCID 18702002HCID 18702002, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

0.254 gram (1.4 mmole, 1.0 eq.) of product from step D was dissolved in 7 ml of 1,2-dichloroethane, after which 0.20 ml of benzoyl chloride and 0.225 gram aluminum (III) chloride (1.7 mmole, 1.2 eq. each) were added. Stirred at room temperature under nitrogen atmosphere for 75 minutes, then quenched with aqueous potassium carbonate. Diluted further with water and extracted 3× with dichloromethane. The combined organics were dried over sodium sulfate, filtered and evaporated. The resulting crude material was chromatographed to give 0.38 gram (95% yield) of the title compound.

Workup

  1. customquenched with aqueous potassium carbonate
  2. additionDiluted further with water
  3. extractionextracted 3× with dichloromethane
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting crude material was chromatographed

Sources & evidence

ORD record
ord-8520ace8b07d46e1af2b392a006ae694
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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