Hydrochloric Acid → 7-(3-Carboxy-1-oxopropyl)-γ-oxo-9H-fluorene-2-butanoic acid

HRID 888700Notes

Reaction equation

HRID 888700 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH:5]1[C:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1.Cl>ClCCCl>[C:21]([CH2:20][CH2:19][C:18]([C:13]1[CH:12]=[CH:11][C:10]2[C:9]3[C:17](=[CH:5][C:6]([C:21](=[O:22])[CH2:20][CH2:19][C:18]([OH:23])=[O:24])=[CH:7][CH:8]=3)[CH2:16][C:15]=2[CH:14]=1)=[O:24])([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6853FluoreneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 587760227-(3-Carboxy-1-oxopropyl)-γ-oxo-9H-fluorene-2-butanoic acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

In a dry agon-purged round bottom flask, anhydrous AlCl3 (98 g, 0.735 mol) was suspended in anhydrous 1,2-dichloroethane (140 mL). In a separate flask, fluorene (23 g, 0.138 mol) was dissolved in anh. 1,2-dichloroethane (125 mL) then added to the AlCl3 suspension. The reaction flask was placed in a room temperature bath and succinic anhydride (34.5 g, 0.345 mol) was carefully added. The reaction was stirred for 16 hours and then very carefully quenched by slow addition to cold 3 M HCl (Caution! The reaction can react violently when HCl is added too rapidly.) The final well mixed suspension was acidic and not reactive to additional HCl solution. The organic solvent was removed at reduced pressure then the product was filtered and washed well with water. The crude product was dissolved in warm NaOH solution (approximately <1M NaOH), filtered and precipitated with the addition of concentrated HCl. The product was filtered, washed with water and then dried at reduced pressure in the presence of P2O5. The product was a pale yellow solid (49.3 g, 97%). 1H-NMR (CD3OD): δ (ppm) 8.3 (s, 2H, Ar); 8.2 (m, 2H, Ar); 8.1 (m, 2H, Ar); 4.1 (s, 2H, CH2); 3.5 (t, 4H, CH2); 2.8 (t, 4H, CH2).

Workup

  1. customIn a dry agon-purged round bottom flask
  2. customwas placed in a room temperature
  3. customvery carefully quenched by slow addition to cold 3 M HCl (Caution
  4. customThe reaction
  5. additionis added too rapidly
  6. addition) The final well mixed suspension
  7. customThe organic solvent was removed at reduced pressure
  8. filtrationthe product was filtered
  9. washwashed well with water
  10. dissolutionThe crude product was dissolved in warm NaOH solution (approximately <1M NaOH),
  11. filtrationfiltered
  12. customprecipitated with the addition of concentrated HCl
  13. filtrationThe product was filtered
  14. washwashed with water
  15. dry with materialdried at reduced pressure in the presence of P2O5

Sources & evidence

ORD record
ord-94413a0bdb7c45b8a681ded6500c4b13
Source dataset
uspto-grants-2012_08
Patent number
US08252275B2

Reaction notes

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