Diethylene Glycol → 9H-fluorene-2-carboxylic acid

HRID 2387648Notes

Reaction equation

HRID 2387648 reaction equation
[C:1]([C:4]1[C:5](=O)[C:6]2[C:14](=[CH:15][CH:16]=1)[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:7]=2)([OH:3])=[O:2].C(O)COCCO.[OH-].[Na+].O.NN>O>[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 66741118HCID 66741118, compound

Product 1

HCID 3485919H-fluorene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

2-Carboxyfluorenone (12.3 g, 0.05 mole) and diethylene glycol were added to a 500 mL round bottom flask. Sodium hydroxide (7.65 g, 0.19 mole) and hydrazine hydrate (9.16 mL, 0.23 mole) were added to the solution. The temperature of the reaction was increased to 125° C. Heating was continued for three hours and then the vessel was cooled to room temperature. Distilled water (1.5 L) was added. The product was precipitated with concentrated hydrochloric acid. The product was filtered and rinsed with distilled water (2 L). The solids were dissolved in 0.5 M sodium hydroxide (2.8 L) and heated to 70° C. The product was precipitated with concentrated hydrochloric acid (pH approximately 2). The product was filtered and washed with distilled water (1.5 L). The 2-carboxyfluorene was dried overnight under reduced pressure with phosphorus pentoxide present. NMR confirmed the structure by the appearance of two new protons at δ4.01 ppm.

Workup

  1. temperatureHeating
  2. temperaturethe vessel was cooled to room temperature
  3. customThe product was precipitated with concentrated hydrochloric acid
  4. filtrationThe product was filtered
  5. washrinsed with distilled water (2 L)
  6. dissolutionThe solids were dissolved in 0.5 M sodium hydroxide (2.8 L)
  7. temperatureheated to 70° C
  8. customThe product was precipitated with concentrated hydrochloric acid (pH approximately 2)
  9. filtrationThe product was filtered
  10. washwashed with distilled water (1.5 L)
  11. dry with materialThe 2-carboxyfluorene was dried overnight under reduced pressure with phosphorus pentoxide present

Sources & evidence

ORD record
ord-8f23f3c0205d416db946d2a83037683e
Source dataset
uspto-grants-2012_09
Patent number
US08268948B2

Reaction notes

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