p-Toluenesulfonic acid → 3,4-Dimethoxy-4'-hydroxychalcone

HRID 394967Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21]CC=C)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

486 mg (1.5 mmol) of 3,4-dimethoxy-4′-allyloxychalcone was dissolved in a mixture of 7.5 ml of methanol and 1.5 ml of water. To the solution were added 150 mg of p-tolu-enesulfonic acid and 150 mg of palladium on carbon (10%) and the solution was heated to 80° C. for 2 h in a sealed flask. The reaction mixture was filtered and poured into a mixture of 10 ml of an aqueous 10% solution of sodium bicarbonate and 10 ml of a saturated aqueous solution of sodium chloride. The mixture was extracted with 15 ml of ethyl acetate and concentrated in vacuo. The residue was recrystallized from methanol to give 0.125 g (25%) of 3,4-dimethoxy-4′-hydroxychalcone (m.p. 193-198° C.) identical to that described by A.v.n Wacek, and E. David, Ber. 70 (1937), 190 (m.p. 208° C.

Workup

filtrationThe reaction mixture was filtered
additionpoured into a mixture of 10 ml of an aqueous 10% solution of sodium bicarbonate and 10 ml of a saturated aqueous solution of sodium chloride
extractionThe mixture was extracted with 15 ml of ethyl acetate
concentrationconcentrated in vacuo
customThe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-c0e2be88bbcd48b4817251b3f4df7315
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603046B1

Reaction notes

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