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

HRID 54714

Reaction equation

HRID 54714 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-d7202d4f58c54fdcb377034cbd137134
Source dataset
uspto-grants-1997_04
Patent number
US05623080

Linked notes

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