Sodium Hydroxide → HCID 69923341, compound

HRID 2416293Notes

Reaction equation

HRID 2416293 reaction equation
[OH-:1].[Na+].[C:3]1(=[O:16])[C:15]2[C:7]([C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:5]=[CH:4]1>C1(C)C(C)=CC=CC=1>[C:7]12([C:11]3[C:12]([C:13]4[C:9]([CH:10]=3)=[CH:9][CH:10]=[CH:11][CH:12]=4)=[CH:13][CH:14]=[CH:15]1)[C:8]1[C:14]([C:15]3[C:7]([CH:8]=1)=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:4]([C:3]([OH:1])=[O:16])[CH:5]=[CH:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22281833Fluoreneone

Product 1

HCID 69923341HCID 69923341, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

 In a 2 l flask, 100 g of fluorenone were dissolved in 1000 ml of dry xylene and admixed while stirring with 200 g of dry NaOH. The mixture was subsequently refluxed for 70 hours. After cooling, the mixture was filtered with suction and the residue was admixed with about 2 l of water. The aqueous suspension was filtered with suction and the precipitate was again slurried with toluene, filtered off with suction and dried. This intermediate was dissolved using about 5 ml of glacial acetic acid per 1 g by refluxing in a 500 ml two-necked flask fitted with reflux condenser and drying tube, 20 ml of concentrated HCl were added and the mixture was refluxed for 5 hours. The reaction mixture was evaporated to about half its volume and was subsequently poured into four times its volume of H2O. The precipitate formed was filtered off with suction, washed well with H2O and dried. To purify it further, it was dissolved at room temperature in an alkaline MeOH/water (10:1) mixture and shaken with toluene. The MeOH/water phase was separated off and, after acidification with hydrochloric acid, poured into water. The spirobifluorene-4-carboxylic acid which was precipitated was filtered off with suction, washed with water and dried.

Workup

  1. temperatureThe mixture was subsequently refluxed for 70 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered with suction
  4. filtrationThe aqueous suspension was filtered with suction
  5. filtrationfiltered off with suction
  6. customdried
  7. dissolutionThis intermediate was dissolved
  8. temperatureby refluxing in a 500 ml two-necked flask
  9. customfitted
  10. temperaturewith reflux condenser
  11. customdrying tube
  12. addition20 ml of concentrated HCl were added
  13. temperaturethe mixture was refluxed for 5 hours
  14. customThe reaction mixture was evaporated to about half its volume
  15. additionwas subsequently poured into four times its volume of H2O
  16. customThe precipitate formed
  17. filtrationwas filtered off with suction
  18. washwashed well with H2O
  19. customdried
  20. customTo purify it further
  21. dissolutionit was dissolved at room temperature in an alkaline MeOH/water (10:1) mixture
  22. customThe MeOH/water phase was separated off
  23. additionafter acidification with hydrochloric acid, poured into water
  24. customThe spirobifluorene-4-carboxylic acid which was precipitated
  25. filtrationwas filtered off with suction
  26. washwashed with water
  27. customdried

Sources & evidence

ORD record
ord-c2c103c46a1b4d62a68b988d50403f08
Source dataset
uspto-grants-2004_11
Patent number
US06822094B2

Reaction notes

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