Diazald → 3-Methoxy-2-(2,4-dichlorobenzoyl)cyclohex-2-enone

HRID 1032235Notes

Reaction equation

HRID 1032235 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].[N+](=[CH2:21])=[N-].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1>CCOCC>[CH3:21][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]

Participants

5

Reactant 3

HCID 6628DiazaldHCID 9550DiazomethaneHCID 143016212-(2,4-Dichlorobenzoyl)cyclohexane-1,3-dione

Product 1

HCID 147965563-Methoxy-2-(2,4-dichlorobenzoyl)cyclohex-2-enoneYield 35%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(2,4-Dichlorobenzoyl)cyclohexane-1,3-dione (2.85 g, 0.01 ml) was stirred as a suspension in 25 ml anhydrous ether. Diazomethane, generated from Diazald™ (50 ml, 0.02 mol) was added at 0° at a rate slow enough to control effervescence. The resulting solution was stirred for an hour and the solvent allowed to evaporated under a stream of nitrogen in a beaker. The resulting oil was dissolved in ether and washed twice with saturated aqueous K2CO3. Evaporation of the solvent under reduced pressure yielded a solid (1.0 g, 35%, m.p. 81°-86° C.), the nuclear magnetic, infrared and mass spectra of which were consistent with the structure.

Workup

  1. additionwas added at 0° at a rate slow enough
  2. customto evaporated under a stream of nitrogen in a beaker
  3. dissolutionThe resulting oil was dissolved in ether
  4. washwashed twice with saturated aqueous K2CO3
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-34697cee103247a9a28655054ec443e7
Source dataset
uspto-grants-1990_09
Patent number
US04957540

Reaction notes

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