Methyl iodide → methyl 9H-xanthene-9-carboxylate

HRID 2121492Notes

Reaction equation

HRID 2121492 reaction equation
[O-][CH2:2]C.[Na+].[Na].[CH:6]1[C:19]2[CH:18]([C:20]([OH:22])=[O:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.CI>O.C(O)C>[CH3:2][O:21][C:20]([CH:18]1[C:19]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:11][C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:22]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 65736Xanthene-9-carboxylic acidHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 699662methyl 9H-xanthene-9-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A sodium ethoxide solution is generated 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 resulting suspension is stirred for 1 hour at ambient temperature. Then the solid is separated off, washed with 1500 mL of diethyl ether, and the isolated crystals are suspended in 1500 mL of dimethylformamide and 126.73 mL (2.0 mol) of methyl iodide is added with stirring. The solution obtained 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. customThen the solid is separated off
  2. washwashed with 1500 mL of diethyl ether
  3. stirringwith stirring
  4. customThe solution obtained
  5. waitis left
  6. waitto stand for 24 hours at ambient temperature
  7. customcrystallized
  8. filtrationsuction filtered
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-aefe8bb9c3184d62aeb7f9fe2686f667
Source dataset
uspto-grants-2004_02
Patent number
US06696462B2

Reaction notes

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