Acetic Acid → HCID 20452425, compound

HRID 1462960Notes

Reaction equation

HRID 1462960 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)[CH:7]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:20][CH:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 4478874HCID 4478874, compound

Product 1

HCID 20452425HCID 20452425, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromo-2-hydroxy-4'-methoxychalcone (16.7 g) was suspended in ethanol (200 ml) and sodium borohydride (3.78 g) added in portions. The resulting solution was stirred for 30 min, then allowed to stand overnight. The solvent was evaporated off, and the residue dissolved in chloroform and washed with water. Evaporation of the solvent gave the crude carbinol intermediate which was boiled under reflux with acetic acid for 2 hr. On cooling, 6-bromo-4'-methoxyflavan crystallised out and was filtered off and dried, 10.2 g, m.p. 121°-123°.

Workup

  1. waitto stand overnight
  2. customThe solvent was evaporated off
  3. dissolutionthe residue dissolved in chloroform
  4. washwashed with water
  5. customEvaporation of the solvent
  6. customgave the crude carbinol intermediate which
  7. temperatureOn cooling
  8. custom6-bromo-4'-methoxyflavan crystallised out
  9. filtrationwas filtered off
  10. customdried

Sources & evidence

ORD record
ord-9943243d27d34517a040a911e77593ee
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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