Hydrochloric Acid → HCID 73177631, compound

HRID 1290456Notes

Reaction equation

HRID 1290456 reaction equation
[C:1]1([CH2:7][CH:8]=[N:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:11].Cl[O-].[Na+]>C(#N)C>[C:1]1([CH2:7][C:8]([Cl:11])=[N:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 99748PhenylacetaldoximeHCID 23665760Sodium Hypochlorite

Product 1

HCID 73177631HCID 73177631, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-5 °C

Procedure

Phenylacetaldehyde oxime (40.5 g, 300 mmol) was dissolved in acetonitrile (100 ml). To the solution, a 6.7% aqueous hydrochloric acid (145 g) and then an 8.5% aqueous sodium hypochlorite (262 g, 299 mmol) were added dropwise at -10° C. over 2.3 hours. The mixture was stirred at -5° C. for 30 minutes and then combined with toluene (200 ml) for extraction. The separated organic layer was washed twice with water (200 ml). Reversed phase HPLC revealed that the extract contained 40.3 g (238 mmol, yield 79%) of the desired compound. The solution was used in the next step without concentration.

Workup

  1. extractioncombined with toluene (200 ml) for extraction
  2. washThe separated organic layer was washed twice with water (200 ml)

Sources & evidence

ORD record
ord-a649e1333b204c5aaf31069c59c1c514
Source dataset
uspto-grants-1998_05
Patent number
US05750717

Reaction notes

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