Benzyl chloroformate → 2-Benzyloxycarbonyloxyimino-2-phenylacetonitrile

HRID 2082997Notes

Reaction equation

HRID 2082997 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]=1

Participants

6

Reactant 4

HCID 10387Benzyl chloroformateHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 699982-(Hydroxyimino)-2-phenylacetonitrile

Product 1

HCID 540061222-Benzyloxycarbonyloxyimino-2-phenylacetonitrileYield 62.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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. 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 n-hexane was added to the residue. The precipitated crystals were collected by filtration to give 2-benzyloxycarbonyloxyimino-2-phenylacetonitrile (5.2 g.), mp 73° to 75° C.

Workup

  1. temperaturecooling
  2. customThe ether layer was separated from the reaction mixture
  3. extractionthe aqueous layer was further extracted with ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. additionn-hexane was added to the residue
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-4514ac63123b4bec82660dbe3aad4207
Source dataset
uspto-grants-1978_04
Patent number
US04083848

Reaction notes

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