Hydrochloric Acid → HCID 73177631, compound

HRID 1604849Notes

Reaction equation

HRID 1604849 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-53b5e03f3c974624a731276c8ac49922
Source dataset
uspto-grants-1999_11
Patent number
US05994558

Reaction notes

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