4-Chloro-benzaldehyde oxime → HCID 19899107, compound

HRID 1196651Notes

Reaction equation

HRID 1196651 reaction equation
Cl[O-].[Na+].[CH:4]1([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9][CH:8]=[CH:7][CH2:6][CH2:5]1.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([CH:20]=[N:21][OH:22])=[CH:18][CH:17]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]2[CH:8]3[CH2:9][CH2:10][CH:4]([C:11]([O:13][CH3:14])=[O:12])[CH2:5][CH2:6][CH:7]3[O:22][N:21]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 2191584-Chloro-benzaldehyde oximeHCID 12630468HCID 12630468, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 19899107HCID 19899107, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

180 ml of 16.38% (w/v) aqueous solution of sodium hypochlorite were added slowly at 5° C. over a period of 6 hours while stirring well to a solution of 61.6 g (0.4 mol) of methyl cyclohept-4-enecarboxylate, 62.0 g (0.4 mol) of 4-chlorobenzaldehyde oxime and 0.5 g of tetrabutylammonium bromide in 800 ml of ethyl acetate. The mixture was held at 20° C. for 2 days. The mixture was then filtered and the organic phase was separated and dried over magnesium sulfate. The solvent was removed by evaporation and the residue was crystallized from diethyl ether/hexane to give 44.65 g of methyl 3-(4-chlorophenyl)-3a,5,6,7,8,8a-hexahydro-4H-cyclohept[d]isoxazole-6-carboxylate as a mixture of two diastereoisomers of melting point 150°-185° C. Isomer A has a melting point of 237°-239° C. and isomer B has a melting point of 162°-166° C.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe residue was crystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-1fa8d537841c451c8b5ed4ccf314c62b
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

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