Resorcinol → Ononetin

HRID 646451Notes

Reaction equation

HRID 646451 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 anhyrous 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) LC retention time 2.39 minutes [M+H]+ 259.2 (Run time 3.75 mins) N.M.R (DMSO-d6) 7.95(d J 8.9 Hz ArH) 7.2(d J 8.7 Hz 2ArH) 6.9(d J 8.7 Hz 2ArH) 6.4(d J 9.9 ArH) 6.25(s ArH) 4.2(s 2CH2) 3.75(s 3OCH3)

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 anhyrous magnesium sulphate
  8. concentrationconcentrated, to a yellow semi-solid

Sources & evidence

ORD record
ord-3ea93b08b42743fdb295944bec271ed4
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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