Benzoyl chloride → HCID 86741278, compound

HRID 235606Notes

Reaction equation

HRID 235606 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[CH3:11][C:12]1[CH:21]=[C:20]([CH3:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[CH:23]1[CH2:28][C:27](=[O:29])[C:26]([C:30](=[N:34][O:35][CH2:36][CH3:37])[CH2:31][CH2:32][CH3:33])=[C:25]([OH:38])[CH2:24]1>CC(C)=O>[C:1]([O:29][C:27]1[CH2:28][CH:23]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]([CH3:22])=[CH:21][C:12]=2[CH3:11])[CH2:24][C:25](=[O:38])[C:26]=1[C:30](=[N:34][O:35][CH2:36][CH3:37])[CH2:31][CH2:32][CH3:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 5360545SodiumHCID 136016126HCID 136016126, compound

Product 1

HCID 86741278HCID 86741278, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A slight excess of benzoyl chloride was added to a suspension of the sodium salt of 5-(2,4-dimethylnaphth-1-yl)-2-[1-(ethoxyimino)butyl]-3-hydroxycyclohex-2-en-1-one (0.34 g) in acetone (20 ml) and the mixture was stirred at room temperqature for 12 hr. The mixture was filtered, the filtrate was evaporated and the residue was purified by column chromatography over silica with dichloromethane elution to give 3-benzoyloxy-5-(2,4-dimethylnaphth-1-yl)-2-[1-(ethoxyimino)butyl]cyclohex-2-en-1-one as a pale yellow oil. The product was characterized by proton nuclear magnetic resonance spectroscopy and the spectroscopic data is recorded in Table 4, Example 10.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customthe residue was purified by column chromatography over silica with dichloromethane elution

Sources & evidence

ORD record
ord-9d275ebee9194f4185bcabdb8cfb7ea3
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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