2-Hydroxychalcone → HCID 610801, compound

HRID 1462957Notes

Reaction equation

HRID 1462957 reaction equation
[OH:1][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][CH:15]=[CH:14][CH:13]=1)=[O:11].[BH4-].[Na+]>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:11]

Participants

4

Reactant 2

HCID 977652-HydroxychalconeHCID 4311764Sodium borohydride

Product 1

HCID 610801HCID 610801, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxychalcone (28.5 g) was stirred with ethanol (500 ml) whilst sodium borohydride (9.45 g) was added in small portions. The solution, which turned from red to pale yellow was allowed to stand overnight at room temperature, then the solvent was evaporated off and the residue extracted with dichloromethane, washing with water. Evaporation of the solvent yielded 3-(o-hydroxyphenyl)-1-phenylpropan-1-ol (24.4 g). 1.0 g of this carbinol was dissolved in concentrated sulphuric acid, and the solution was allowed to stand at room temperature for 2 hr. The solution was poured into iced water, and the sticky orange product filtered off, washed with water, dried, and chromatographed on alumina, eluting with toluene. Evaporation of the eluate gave flavan (0.20 g), which was recrystallised from petroleum ether, b.p. 40°-60°, to give flavan m.p. 42°-43°.

Workup

  1. additionwas added in small portions
  2. customthe solvent was evaporated off
  3. extractionthe residue extracted with dichloromethane
  4. washwashing with water
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d6c97739b14442f7834c0aa3994c47ec
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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