Methyl Salicylate → 3-Hydroxyxanthen-9-one

HRID 1088480Notes

Reaction equation

HRID 1088480 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9](OC)(=[O:17])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)O>>[OH:2][C:1]1[CH:8]=[CH:7][C:6]2[C:9](=[O:17])[C:10]3[C:11]([O:5][C:4]=2[CH:3]=1)=[CH:13][CH:14]=[CH:15][CH:16]=3

Participants

3

Reactant 2

HCID 4133Methyl SalicylateHCID 5054Resorcinol

Product 1

HCID 53760133-Hydroxyxanthen-9-oneYield 12.3%

Procedure

Resorcinol (5.5 g, 50 mmol) and methyl salicylate (11.0 g, 72 mmol) were refluxed for 5 h using a Dean-Stark trap to remove H2O and MeOH. The resulting black oil was chromatographed over silica with 20% ethyl acetate-hexane as eluent. A yellow solid was isolated which was subsequently recrystallized from ethyl acetate to give 1.3 g (12.3%) of 3-hydroxy-9H-xanthen-9-one (lit. mp 242° C.). Literature references to the synthesis of this compound: R. J. Patolia and K. N. Trivedi, Indian J. Chem., 22B, 444 (1983); J. S. H. Davies, F. Scheinmann, and H. Suschitzky, J. Org. Chem., 23, 307 (1958). ##STR37##

Workup

  1. customto remove H2O and MeOH
  2. customThe resulting black oil was chromatographed over silica with 20% ethyl acetate-hexane as eluent
  3. customA yellow solid was isolated which
  4. customwas subsequently recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-51fc9ea9a9064ce4a9860f6a5164bdaf
Source dataset
uspto-grants-1990_10
Patent number
US04962192

Reaction notes

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