Acetone → 3,4-Bis-allyloxyxanthen-9-one

HRID 734181Notes

Reaction equation

HRID 734181 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[C:15]=1[OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH2:18](Br)[CH:19]=[CH2:20].O.C(=O)([O-])[O-].[K+].[K+].[CH3:29][C:30]([CH3:32])=O>ClCCl>[CH2:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[C:15]=1[O:16][CH2:32][CH:30]=[CH2:29])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:19]=[CH2:20]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 57483823,4-Dihydroxy-xanthoneHCID 21835276Potassium carbonate hydrate

Product 1

HCID 161050373,4-Bis-allyloxyxanthen-9-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3,4-dihydroxyxanthen-9-one (290 mg, 1.27 mmol), allyl bromide (800 μL, 9.20 mmol), potassium carbonate hydrate (1.28 g, 7.77 mmol) and acetone (15.0 mL) was refluxed for 2.5 h. The solution was cooled to room temperature and dichloromethane was added. The mixture was filtered and the filtrate was rotary evaporated to yield 372 mg (95%) of the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz): δ 8.33 (dd, J1=7.84 Hz, J2=1.79, 1H), 8.07 (d, J=8.79 Hz, 1H), 7.72 (ddd, J1=8.10 Hz, J2=7.01, J3=1.65, 1H), 7.56 (dd, J1=8.51 Hz, J2=0.55, 1H), 7.38 (ddd, J1=7.76 Hz, J2=7.07, J3=1.03, 1H), 7.00 (d, J=9.06 Hz, 1H), 6.15 (m, 2H), 5.48 (m, 1H), 5.38 (m, 2H), 5.25 (m, 1H), 4.74 (m, 4H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was rotary evaporated

Sources & evidence

ORD record
ord-6404795bc2044cb6ae539d6735e63dab
Source dataset
uspto-grants-2009_09
Patent number
US07592143B2

Reaction notes

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