Acetic Acid → HCID 20452420, compound

HRID 1462961Notes

Reaction equation

HRID 1462961 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[CH3:19])=[O:11].[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH3:19][C:13]1[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]=1[CH:10]1[CH2:9][CH2:8][C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:2]=2)[O:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 367352HCID 367352, compoundHCID 4311764Sodium borohydride

Product 1

HCID 20452420HCID 20452420, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxy-2',4'-dimethylchalcone (8.20 g) was suspended in ethanol (150 ml) and sodium borohydride (2.50 g) was added in portions. The mixture was stirred for 30 min and the resulting solution allowed to stand overnight. The solvent was distilled off and the residue dissolved in chloroform and washed with water. Evaporation of the chloroform gave the crude intermediate carbinol which was boiled under reflux with acetic acid (100 ml) for 2 hr. Evaporation gave an oily residue which was chromatographed on alumina, eluting with toluene. The main fraction, on evaporation of the solvent, was distilled under vacuum to give 2',4'-dimethylflavan, 4.80 g, b.p. 135°-145°/0.8 mm. Hg=107 Pa.

Workup

  1. waitto stand overnight
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue dissolved in chloroform
  4. washwashed with water
  5. customEvaporation of the chloroform
  6. customgave the crude intermediate carbinol which
  7. customEvaporation
  8. customgave an oily residue which
  9. customwas chromatographed on alumina
  10. washeluting with toluene
  11. customThe main fraction, on evaporation of the solvent
  12. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-27d6aa04c78d4698a084a789ca8f363f
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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