Sodium Hydroxide → 9-Methyl-9H-fluorene-9-carboxylic acid

HRID 33417Notes

Reaction equation

HRID 33417 reaction equation
[CH3:1][C:2]1([C:15]([O:17]C)=[O:16])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[OH-].[Na+]>O1CCOCC1>[CH3:1][C:2]1([C:15]([OH:17])=[O:16])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14934655Methyl 9-methylfluorene-9-carboxylate

Product 1

HCID 35878029-Methyl-9H-fluorene-9-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

12.6 g (0.053 mol) of methyl 9-methylfluorene-9-carboxylate and 53 mL of 2 molar, aqueous sodium hydroxide solution are stirred in 120 mL of 1,4-dioxane for 24 hours at ambient temperature. The dioxane is distilled off, made up to a total volume of 300 mL with water, and extracted with diethyl ether. The aqueous phase is acidified with 3 molar aqueous HCl, crystallized, and filtered. Yield: 11.25 g of white crystals (95% of theoretical yield); melting point: 168° C.-169° C.

Workup

  1. distillationThe dioxane is distilled off
  2. extractionextracted with diethyl ether
  3. customcrystallized
  4. filtrationfiltered

Sources & evidence

ORD record
ord-5114c2bbbba84cb9b146c2e7c054fcea
Source dataset
uspto-grants-2008_09
Patent number
US07429600B2

Reaction notes

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