2,2',4,4'-Tetrahydroxybenzophenone → 3,6-dihydroxy-9H-xanthen-9-one

HRID 2399639Notes

Reaction equation

HRID 2399639 reaction equation
O[C:2]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[OH:13])=[O:5]>O>[OH:18][C:16]1[CH:17]=[CH:2][C:3]2[C:4](=[O:5])[C:6]3[C:7]([O:13][C:14]=2[CH:15]=1)=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=3

Participants

3

Reactant 1

HCID 85712,2',4,4'-Tetrahydroxybenzophenone

Product 1

HCID 57493223,6-dihydroxy-9H-xanthen-9-oneYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2',4,4'-Tetrahydroxybenzophenone (2.5 g, 10.15 mmol.) was heated in 20 ml of water at 195°-200° C. for 4 hours (Aldrich pressure tube). After cooling, the crude product was filtered off and mixed with 25 ml of water. The resulting suspension was refluxed for 25 min. and filtered at about 60° C. Pure product 3,6-dihydroxyxanthone 2.15 g was obtained in 90.4% yield. It did not melt below 330° C. HNMR (DMSO): 10.780 (s,2H), 7.983 (d,2H,J=8.6 Hz), 6,822 (m,4H). MS: 228,220, 1717, 115, 100, 69, 63.

Workup

  1. temperatureAfter cooling
  2. filtrationthe crude product was filtered off
  3. additionmixed with 25 ml of water
  4. temperatureThe resulting suspension was refluxed for 25 min.
  5. filtrationfiltered at about 60° C

Sources & evidence

ORD record
ord-71fdf0a7bfa64a0dafc33c12524381fe
Source dataset
uspto-grants-1995_09
Patent number
US05451343

Reaction notes

Loading…