Benzophenone, 2,2',5-trimethoxy- → 2-Hydroxyxanthone

HRID 1464583Notes

Reaction equation

HRID 1464583 reaction equation
CO[C:3]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13]C)=[O:6].Cl.N1C=CC=CC=1>>[OH:19][C:16]1[CH:17]=[CH:18][C:3]2[O:13][C:8]3[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5](=[O:6])[C:4]=2[CH:15]=1

Participants

3

Reactant 2

HCID 36279Benzophenone, 2,2',5-trimethoxy-HCID 10176127Pyridinium chloride

Product 1

HCID 747082-Hydroxyxanthone

Procedure

A mixture of crude 2,2',5-trimethoxybenzophenone (22.6 g, 83 mmol) prepared as described above, and pyridine hydrochloride (121 g, 1.04 mol) was refluxed (~210° C.) for 10 hours under N2. The mixture was then poured into ice water (350 g), and the resultant yellow-green precipitate was collected by filtration and washed with water (2×100 mL), and 6 N aqueous HCl (3×100 mL), and dried in vacuo. Yield: 14.1 g (80%). TLC: Rf 0.54 [benzene-EtOH (20:3)]. m.p. 245°-246° C. NMR data in accordance with structure. ##STR4##

Workup

  1. customprepared
  2. temperaturewas refluxed (~210° C.) for 10 hours under N2
  3. filtrationthe resultant yellow-green precipitate was collected by filtration
  4. washwashed with water (2×100 mL), and 6 N aqueous HCl (3×100 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8ab3ecadc9bc4a3a89d4668d0170cd90
Source dataset
uspto-grants-1994_04
Patent number
US05306562

Reaction notes

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