Acetic Acid → HCID 11666638, compound

HRID 498976Notes

Reaction equation

HRID 498976 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)=O.[BH4-].[Na+].C(O)(=[O:27])C>C(O)CC>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:27])[CH2:10][CH2:11][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 68461836HCID 68461836, compound

Product 1

HCID 11666638HCID 11666638, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Dihydroxy-3′,4′-dimethoxychalcone (4) (40 mg) was dissolved in 1-propanol (5 ml), followed by the addition of sodium borohydride (15 mg) and the mixture was allowed to react at room temperature for 2 hours. Upon completion of the reaction, 20% acetic acid (0.2 ml) was added and the mixture was heated at 80° C. for 5 minutes and cooled down. The mixture was then separated on a pre-packed C18 column eluting with a MeOH/H2O gradient to provide 1-(2,4-dihydroxyphenyl)-3-(3,4-dimethoxyphenyl)-1-propanol (5). The structure of compound (5) was confirmed by MS, UV spectroscopy, 1D and 2D 1H-NMR.

Workup

  1. customto react at room temperature for 2 hours
  2. additionwas added
  3. temperaturecooled down
  4. customThe mixture was then separated on a pre-packed C18 column
  5. washeluting with a MeOH/H2O gradient

Sources & evidence

ORD record
ord-aa54ebc48d824430b21527073e9c4b12
Source dataset
uspto-grants-2010_08
Patent number
US07767661B2

Reaction notes

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