Benzyl chloroformate → 2-Benzyloxycarbonyloxyimino-2-phenylacetonitrile
Reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH:12][N:13]=[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:15]#[N:16].[OH-].[K+].O1CCOCC1>CCOCC>[CH2:5]([O:4][C:2]([O:12][N:13]=[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:15]#[N:16])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Procedure
A solution of benzyl chloroformate (5.1 g.) in ether (40 ml.) was added to a solution of 2-hydroxyimino-2-phenylacetonitrile (4.4 g.) in a mixture of a 1N potassium hydroxide aqueous solution (30 ml.) and dioxane (10 ml.) under ice-cooling, and the mixture was stirred for 1 hour at the same temperature and for 4 hours at room temperature. The ether layer was separated from the reaction mixture and the aqueous layer was further extracted with ether. Both ether layers were combined, washed with water and dried over magnesium sulfate. The solvent was distilled off and to the residue was added n-hexane. The precipitated crystals were collected by filtration to give 2-benzyloxycarbonyloxyimino-2-phenylacetonitrile (5.2 g.), mp 73° to 75° C.
Workup
- temperaturecooling
- customThe ether layer was separated from the reaction mixture
- extractionthe aqueous layer was further extracted with ether
- washwashed with water
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off and to the residue
- additionwas added n-hexane
- filtrationThe precipitated crystals were collected by filtration
Sources & evidence
- ORD record
- ord-f63af131f3ad45978fb060695b4bd757
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04010178
Reaction notes
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