Potassium Hydroxide → 2-(9H-fluoren-2-yl)acetic acid

HRID 1729890Notes

Reaction equation

HRID 1729890 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=O)[C:15]([OH:17])=[O:16].[OH-].[K+]>O.NN>[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21406504Fluorene-2-glyoxylic acid

Product 1

HCID 232711852-(9H-fluoren-2-yl)acetic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

A suspension of fluorene-2-glyoxylic acid (33.7 g) in hydrazine hydrate (50 ml) is refluxed until solution is achieved, cooled and treated with potassium hydroxide (33.7 g) in portions. The mixture is then refluxed for 1 hour, and the excess hydrazine removed by distillation. The residue is dissolved in water and extracted with chloroform. The aqueous layer is acidified to pH 2.0 with 10% HCl and extracted with ether. The ether extracts are washed, dried (MgSO4) and evaporated to give the title compound (29.7 g, mp 184°-186°).

Workup

  1. temperatureis refluxed until solution
  2. temperaturecooled
  3. temperatureThe mixture is then refluxed for 1 hour
  4. customthe excess hydrazine removed by distillation
  5. dissolutionThe residue is dissolved in water
  6. extractionextracted with chloroform
  7. extractionextracted with ether
  8. washThe ether extracts are washed
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-0de935ce65dd4a59a6b3a0d20bce9d7e
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

Loading…