Phenol → 1,3,5-Trihydroxyxanthone

HRID 1602675

Reaction equation

HRID 1602675 reaction equation
C[O:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[C:10]([O:18]C)[CH:11]=[CH:12][CH:13]=3)[O:8][C:7]=2[CH:6]=[C:5]([O:20]C)[CH:4]=1.C1(O)C=CC=CC=1.I.OS([O-])=O.[Na+]>>[OH:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[C:10]([OH:18])[CH:11]=[CH:12][CH:13]=3)[O:8][C:7]=2[CH:6]=[C:5]([OH:20])[CH:4]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 24841Hydrogen iodideHCID 119533681,3,5-TrimethoxyxanthoneHCID 23665763Sodium Bisulfite

Product 1

HCID 52816631,3,5-Trihydroxyxanthone

Conditions

Temperature
160 °C

Procedure

A mixture of compound 19 (1.9 g, 6.64 mmol) phenol (42 ml) and HI (35 ml) was refluxed at 160° C. for 8 hour and the reaction mixture was poured into aqueous NaHSO3 solution. The resulting yellow precipitate, was collected, purified by silica gel column chromatography (CH2Cl2 --MeOH, 4:1), and crystallized from methanol to give pale yellow needles 20, 1.41 g (5.78 mmol, 87%).

Workup

  1. customThe resulting yellow precipitate, was collected
  2. custompurified by silica gel column chromatography (CH2Cl2 --MeOH, 4:1)
  3. customcrystallized from methanol

Sources & evidence

ORD record
ord-6001ba9a298d4a4f9e40bc3475f83e36
Source dataset
uspto-grants-1999_11
Patent number
US05981774

Linked notes

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