Acetone → HCID 22748764, compound

HRID 1390338Notes

Reaction equation

HRID 1390338 reaction equation
C(C1[CH:14]=[CH:13][C:12]([CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][N:10]=1)=CC1C=CC=CC=1.[Mn]([O-])(=O)(=O)=[O:29].[K+].C[C:35]([CH3:37])=[O:36]>>[C:16]1([CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:12]2[CH:13]=[CH:14][C:37]([C:35]([OH:29])=[O:36])=[N:10][CH:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 53712498HCID 53712498, compound

Product 1

HCID 22748764HCID 22748764, compound

Procedure

A mixture of 8.2 g. 2-styryl-5-(diphenylmethyl)-pyridine and 120 ml. of acetone is cooled to -10° C. and with vigorous stirring 6.66 g. of finely divided potassium permanganate is added slowly, in a portion-wise fashion, over a 1.5 hour period whilst maintaining the temperature below -5° C. Allow the mixture to stand at -15° C. for 15 hours, filter and wash the solids with chloroform and extract three times with 150 ml. of boiling water. Acidify the aqueous extracts with hydrochloric acid and extract with ether. Discard the ether extracts and basify the aqueous phase to pH 2.5 and filter and dry the precipitated acid which is recrystallized from ethanol to yield the tiltle product (m.p. 189°-191° C.).

Workup

  1. additionA mixture of 8.2 g
  2. temperaturewhilst maintaining the temperature below -5° C
  3. filtrationfilter
  4. washwash the solids with chloroform
  5. extractionextract three times with 150 ml
  6. extractionextract with ether
  7. filtrationfilter
  8. customdry the precipitated acid which
  9. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-7fbade96ae554993b1428a5a6ea68ab5
Source dataset
uspto-grants-1979_02
Patent number
US04138488

Reaction notes

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