Ethanol → methyl 9H-xanthene-9-carboxylate

HRID 750546Notes

Reaction equation

HRID 750546 reaction equation
[Na].[CH2:2](O)C.[CH:5]1[C:18]2[CH:17]([C:19]([OH:21])=[O:20])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.CI>O>[CH:15]1[C:16]2[CH:17]([C:19]([O:21][CH3:2])=[O:20])[C:18]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[O:10][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 65736Xanthene-9-carboxylic acidHCID 5360545Sodium

Product 1

HCID 699662methyl 9H-xanthene-9-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sodium ethoxide solution is prepared from 21.75 g (0.95 mol) of sodium and 1500 mL of ethanol. 214 g (0.95 mol) of xanthene-9-carboxylic acid is added batchwise to this solution and the suspension obtained is stirred for 1 hour at ambient temperature. Then the solid is separated off, washed with 1500 mL diethyl ether, and the isolated crystals are suspended in 1500 mL of dimethylformamide and combined with 126.73 mL (2.0 mol) of methyl iodide with stirring. The solution formed is left to stand for 24 hours at ambient temperature, then diluted with water to a total volume of 6 L, crystallized, suction filtered, washed with water, and dried. Yield: 167 g of white crystals (74% of theoretical yield); melting point: 82° C.

Workup

  1. customthe suspension obtained
  2. customThen the solid is separated off
  3. washwashed with 1500 mL diethyl ether
  4. stirringwith stirring
  5. customThe solution formed
  6. waitis left
  7. waitto stand for 24 hours at ambient temperature
  8. customcrystallized
  9. filtrationsuction filtered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-65a3a5c44d624383882ecfdb9b104e44
Source dataset
uspto-grants-2008_07
Patent number
US07405224B2

Reaction notes

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