Acetic Acid → HCID 10867936, compound

HRID 1462948Notes

Reaction equation

HRID 1462948 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[CH2:3][CH:2]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18](O)(=O)C>Cl>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([CH:2]2[CH2:3][CH2:4][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[O:1]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 10251Flavanone

Product 1

HCID 10867936HCID 10867936, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

The crude flavanone was dissolved in a mixture of acetic acid (200 ml.) and concentrated hydrochloric acid (45 ml.), warmed to 50° C., and added to wet zinc amalgam (prepared from 60 g. zinc powder and 6 g. mercuric acetate). The mixture was swirled for 15 mins., allowed to stand for 30 mins., then heated on the steam bath for 15 mins. The residual zinc was filtered off and the filtrate diluted with water. The crude product was extracted into toluene and the extract washed with water and saturated sodium bicarbonate solution. Evaporation gave a residue which was chromatographed on alkaline, alumina, eluting with toluene. The first fraction obtained on evaporation of the solvent was recrystallised from ethanol to yield 4'-methylflavan (1.4 g.). m.p. 94° C.

Workup

  1. waitto stand for 30 mins
  2. temperature, then heated on the steam bath for 15 mins
  3. filtrationThe residual zinc was filtered off
  4. additionthe filtrate diluted with water
  5. extractionThe crude product was extracted into toluene
  6. washthe extract washed with water and saturated sodium bicarbonate solution
  7. customEvaporation
  8. customgave a residue which
  9. customwas chromatographed on alkaline, alumina
  10. washeluting with toluene
  11. customThe first fraction obtained on evaporation of the solvent
  12. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-0992b468be6a44a594ee12e196cbf705
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

Loading…