Hydrochloric Acid → Mls003115290

HRID 1580155Notes

Reaction equation

HRID 1580155 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[C:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[OH:23]O.Cl>O.C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]2[O:23][C:8]32[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]3=[O:18])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 6212ChloroformHCID 27327162-(Pyridin-4-ylmethylidene)-3,4-dihydronaphthalen-1-one

Product 1

HCID 317204Mls003115290

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 10 g. of 2-(4-pyridylmethylene)-3,4-dihydro-1(2H)-naphthalenone in 100 ml of water and 200 ml of ethanol is added sufficient chloroform to dissolve the reactants. The pH is adjusted to between 7 and 9 and a 3 molar excess of 30% hydrogen peroxide in water is added dropwise at room temperature. The reactants are stirred for 5 hours after which sufficient ferrous sulfate is added to neutralize the excess peroxide. The mixture is then acidified with hydrochloric acid and the organic solvent evaporated off. The water solution remaining is made basic and extracted with chloroform. The chloroform is evaporated off yielding 3'-(4-pyridyl)-spiro[1,2,3,4-tetrahydronaphthalene-2,2'-oxirane]-1-one.

Workup

  1. additionTo a mixture of 10 g
  2. dissolutionto dissolve the reactants
  3. additionis added
  4. customthe organic solvent evaporated off
  5. extractionextracted with chloroform
  6. customThe chloroform is evaporated off

Sources & evidence

ORD record
ord-45e33bef9cce45a896b4ce25722ebd81
Source dataset
uspto-grants-1976_01
Patent number
US03932430

Reaction notes

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