Benzoyl chloride → HCID 86741278, compound

HRID 2118862Notes

Reaction equation

HRID 2118862 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 temperature for 12 hr. The mixture was filtered, the filtrate was evaporated and the residue was purified by column chromatography overe 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 overe silica with dichloromethane elution

Sources & evidence

ORD record
ord-b0735871f4db48bf91086fdb7f75bedd
Source dataset
uspto-grants-1987_07
Patent number
US04680400

Reaction notes

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