Resorcinol → Ononetin

HRID 2097237Notes

Reaction equation

HRID 2097237 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=[O:19])=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+]>B(F)(F)F>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[C:18](=[O:19])[CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 76904-Methoxyphenylacetic AcidHCID 517045Sodium Acetate

Product 1

HCID 259632Ononetin

Reagents, catalysts & solvents 1

HCID 6356Boron trifluorideSolvent

Conditions

Temperature
90 °C

Procedure

Resorcinol (4.4 g, 40 mmol) and 4-methoxyphenylacetic acid (6.6 g, 40 mmol) in boron trifluoride.etherate (25 ml, 0.2 mol) was heated, under a nitrogen atmosphere, at 90° C. for ˜90 mins. to give a pale red solution. The solution was allowed to cool and poured into aqueous sodium acetate (200 ml, 10%) and the mixture stirred to give a pale yellow precipitate. The solids were removed by filtration and washed with water (200 ml). Solids were taken up in ethyl acetate (250 ml) and washed with water (200 ml). Solution was dried over anhydrous magnesium sulphate and concentrated, to a yellow semi-solid. Trituration with diethyl ether (100 ml) gave the 1-(2,4-dihydroxy-phenyl)-2-(4-methoxy-phenyl)-ethanone as a pale orange solid, dried in vacuo, (2.2 g)

Workup

  1. customto give a pale red solution
  2. temperatureto cool
  3. customto give a pale yellow precipitate
  4. customThe solids were removed by filtration
  5. washwashed with water (200 ml)
  6. washwashed with water (200 ml)
  7. dry with materialSolution was dried over anhydrous magnesium sulphate
  8. concentrationconcentrated, to a yellow semi-solid

Sources & evidence

ORD record
ord-9352dafcc57f48ab8d064d3eded27adf
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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