Sulfuric Acid → HCID 19353608, compound

HRID 362553Notes

Reaction equation

HRID 362553 reaction equation
Cl[O-].[Na+].[CH2:4]([O:11][C:12]1[CH:23]=[CH:22][C:15]([CH:16]=[C:17]([C:20]#[N:21])[C:18]#[N:19])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.S(=O)(=O)(O)[OH:25]>O1CCOCC1>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH:16]2[O:25][C:17]2([C:20]#[N:21])[C:18]#[N:19])=[CH:22][CH:23]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 33804Malononitrile, (p-(benzyloxy)benzylidene)-HCID 23665760Sodium Hypochlorite

Product 1

HCID 19353608HCID 19353608, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.3 ml of 1.2M aqueous sodium hypochloride solution were added dropwise to a suspension of 1.04 g (4 mmol) of 2-(4-benzyloxybenzylidene)-malononitrile in 12 ml of dioxan while stirring at pH 9-10, the mixture was stirred at room temperature for 1 hour and 2N sulphuric acid was added until a pH of 4.8 was reached. Extraction with ethyl acetate, drying with sodium sulphate and distillation of the solvent gave 1.22 g of 3-(4-benzyloxyphenyl)-oxirane-2,2-dicarbonitrile as a yellow-brown oil, which was used without further purification for the next step.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying with sodium sulphate and distillation of the solvent

Sources & evidence

ORD record
ord-f9d4c964f6434b279789fe3d147c68c0
Source dataset
uspto-grants-1999_02
Patent number
US05869500

Reaction notes

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