Sodium Hydroxide → 9H-Fluoren-9-ylideneacetic acid

HRID 886814Notes

Reaction equation

HRID 886814 reaction equation
C([O:3][C:4](=[O:19])[CH:5]=[C:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)C.[OH-].[Na+]>CCO>[CH:17]1[C:18]2[C:6](=[CH:5][C:4]([OH:19])=[O:3])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 282552Ethyl 9-fluorenylideneacetate

Product 1

HCID 967929H-Fluoren-9-ylideneacetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

1.85 g (7.39 mmol, 1 eq) of 4 are introduced into 40 mL of EtOH. 14.8 mL (14.78 mmol, 2 eq) of 1 N sodium hydroxide are added and the mixture is stirred for 45 min at 60° C. The reagent dissolves completely while hot. The ethanol is concentrated, the residue is taken up in the water and AcOEt is added. The aqueous phase is acidified to pH 3, then extracted with AcOEt. The organic phase is washed with brine, dried, filtered and concentrated (m=1.62 g, yield=99%).

Workup

  1. dissolutionThe reagent dissolves completely while hot
  2. concentrationThe ethanol is concentrated
  3. additionis added
  4. extractionextracted with AcOEt
  5. washThe organic phase is washed with brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated (m=1.62 g, yield=99%)

Sources & evidence

ORD record
ord-696ecfcf41164a559dca588281af2732
Source dataset
uspto-grants-2012_08
Patent number
US08247412B2

Reaction notes

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