Water → Tropenol 9-hydroxyxanthene-9-carboxylate

HRID 750548Notes

Reaction equation

HRID 750548 reaction equation
[OH:1][C:2]1([C:16]([O:18]C)=[O:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[C@@:20]12([OH:29])[N:27]([CH3:28])[C@@H:24]([CH2:25][CH2:26]1)[CH2:23][CH:22]=[CH:21]2.[Na].O>C(#N)C>[C@@:20]12([OH:29])[N:27]([CH3:28])[C@@H:24]([CH2:25][CH2:26]1)[CH2:23][CH:22]=[CH:21]2.[OH:1][C:2]1([C:16]([O-:18])=[O:17])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[O:9][C:10]2[C:15]1=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

6

Reactant 4

HCID 962WaterHCID 5360545Sodium2×HCID 12068826Methyl 9-hydroxyxanthene-9-carboxylateHCID 53629842Tropenol

Product 1

HCID 86760722Tropenol 9-hydroxyxanthene-9-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.65 g (0.053 mol) of methylester 3a, 8.35 g (0.06 mol) of tropenol and 0.2 g of sodium are heated as a melt at 75 mbar for 4 hours over a bath of boiling water with occasional agitation. After cooling, the sodium residues are dissolved with acetonitrile, the solution is evaporated to dryness, and the residue is extracted with dichloromethane/water. Then the organic phase is washed with water, dried over magnesium sulfate, and the solvent is distilled off. The product is purified by recrystallization from diethyl ether/petroleum ether. Yield: 5.28 g of white crystals (27% of theoretical yield); melting point: 117° C.

Workup

  1. temperatureAfter cooling
  2. customthe solution is evaporated to dryness
  3. extractionthe residue is extracted with dichloromethane/water
  4. washThen the organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent is distilled off
  7. customThe product is purified by recrystallization from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-f6d8bf991b9d4c6384e2702cc154ce96
Source dataset
uspto-grants-2008_07
Patent number
US07405224B2

Reaction notes

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