Hydrochloric Acid → HCID 13270920, compound

HRID 1462950Notes

Reaction equation

HRID 1462950 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]2[CH2:15][C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]2)=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2420652-(4-CHLOROPHENYL)CHROMAN-4-ONE

Product 1

HCID 13270920HCID 13270920, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4'-Chloroflavanone (4.0 g.) was dissolved in acetic acid (150 ml.) and concentrated hydrochloric acid (20 ml.) and added to wet zinc amalgam (prepared from zinc powder (80 g.) and mercuric chloride (6.4 g.)). The reaction mixture was stirred for 1 hr. then allowed to stand overnight. The residual zinc was filtered off and washed with water, and the filtrate and washings combined and diluted with water. The oily product was extracted into ether, and the extract washed with water and saturated sodium bicarbonate solution; it was dried with magnesium sulphate, filtered and evaporated, and the residue chromatographed on alkaline alumina, eluting with toluene. The eluate was evaporated and the residue recrystallised from ethanol, to give 4'-chloroflavan, m.p. 76°-77° C.

Workup

  1. waitto stand overnight
  2. filtrationThe residual zinc was filtered off
  3. washwashed with water
  4. additiondiluted with water
  5. extractionThe oily product was extracted into ether
  6. washthe extract washed with water and saturated sodium bicarbonate solution
  7. dry with materialit was dried with magnesium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customthe residue chromatographed on alkaline alumina
  11. washeluting with toluene
  12. customThe eluate was evaporated
  13. customthe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-5bfbe44a81884441b92f7d60ae5bca41
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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