Sodium → HCID 13393819, compound

HRID 978784Notes

Reaction equation

HRID 978784 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19].Cl([O-])=[O:21].[Na+].[Na]>C(O)(C)(C)C.CC(=CC)C.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:3]=1[C:18]([OH:21])=[O:19]

Participants

7

Reactant 3

HCID 5360545SodiumHCID 13393783HCID 13393783, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 13393819HCID 13393819, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

To a stirred solution of 5.8 g 4-chloro-3-formyl-flav-3-ene in 500 ml tert-butanol and 100 ml 2-methylbut-2-ene at room temperature is added dropwise a solution of 17.9 g sodium chlorite and 17.9 g sodium dihydrogenophosphate in 200 ml water. Stirring is continued for 5 hours. The solution is concentrated in vacuo and water is added to the residue to give a suspension. The mixture is extracted with hexane and the clear organic extracts are discarded. Subsequently, the aqueous suspension is acidified to pH 3 and the mixture is extracted with chloroform. The combined chloroform extracts are washed with water, dried over magnesium sulfate, filtered and evaporated. The residual solid is recrystallized in a mixture of chloroform and hexane. Pure 4-chloro-3-carboxy-flav-3-ene is obtained as yellow crystals; m.p. 210° C.

Workup

  1. concentrationThe solution is concentrated in vacuo and water
  2. additionis added to the residue
  3. customto give a suspension
  4. extractionThe mixture is extracted with hexane
  5. extractionthe mixture is extracted with chloroform
  6. washThe combined chloroform extracts are washed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residual solid is recrystallized in a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-cff2c199bc4c43728996748705fcce94
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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