Pyridine → HCID 14796557, compound

HRID 2073665Notes

Reaction equation

HRID 2073665 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]1=[O:13])=[O:5].[C:19](Cl)(=[O:21])[CH3:20].N1C=CC=CC=1>CCOCC>[C:19]([O:12][C:11]1[CH2:10][CH2:9][CH2:8][C:7](=[O:13])[C:6]=1[C:4](=[O:5])[C:3]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:2]=1[Cl:1])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 143016212-(2,4-Dichlorobenzoyl)cyclohexane-1,3-dione

Product 1

HCID 14796557HCID 14796557, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(2,4-Dichlorobenzoyl)cyclohexane-1,3-dione (11.4 g, 0.04 mol), acetyl chloride (3.15 g, 0.041 mol) and pyridine (3.2 g, 0.041 mol) were mixed in 100 ml ether and stirred at room temperature for 24 hours. The volatiles were evaporated under reduced pressure, and water and CH2Cl2 were added. The organic layer was then washed three times each with 1N HCl and then 5% Na2CO3, dried with MgSO4 and the solvent evaporated under reduced pressure to yield the product, 8.4 g, 64%. The structure was confirmed as such by nuclear magnetic, infrared and mass spectroscopy.

Workup

  1. customThe volatiles were evaporated under reduced pressure, and water and CH2Cl2
  2. additionwere added
  3. washThe organic layer was then washed three times each with 1N HCl
  4. dry with material5% Na2CO3, dried with MgSO4
  5. customthe solvent evaporated under reduced pressure
  6. customto yield the product, 8.4 g, 64%

Sources & evidence

ORD record
ord-399fa1a29d68419887611abfb0dc2bf8
Source dataset
uspto-grants-1990_04
Patent number
US04918236

Reaction notes

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