HCID 284115, compound → HCID 20452411, compound

HRID 1462959Notes

Reaction equation

HRID 1462959 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][C:15]([O:18][CH3:19])=[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][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[OH:11]

Participants

4

Reactant 2

HCID 284115HCID 284115, compoundHCID 4311764Sodium borohydride

Product 1

HCID 20452411HCID 20452411, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Hydroxy-4'-methoxychalcone (12.7 g) was stirred with ethanol (200 ml) and sodium borohydride (3.8 g) added in portions. The solution was stirred at room temperature, the solvent evaporated, and the residue washed with water and recrystallised from aqueous ethanol to give 3-(o-hydroxyphenyl)-1-(p-methoxyphenyl)propan-1-ol (8.60 g), m.p. 114°-116°. The total product was boiled under reflux with acetic acid (100 ml) for 2 hr., the solution evaporated, and the residue chromatographed on alumina, eluting with toluene, to yield 4'-methoxyflavan (8.0 g), m.p. 82°-83°.

Workup

  1. additionadded in portions
  2. customthe solvent evaporated
  3. washthe residue washed with water
  4. customrecrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-7cfe63c84dff4b2f82102abcfee3e8a6
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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