Pyridine → HCID 23126022, compound

HRID 132728

Reaction equation

HRID 132728 reaction equation
[OH:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.N1C=CC=CC=1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:33](Cl)(=[O:36])[CH2:34][CH3:35]>O.O1CCCC1>[C:24]([O:1][CH2:2][C:3]1([CH2:16][O:17][C:33](=[O:36])[CH2:34][CH3:35])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 7412Benzoyl chlorideHCID 62324Propionyl chlorideHCID 3450229H-Fluorene-9,9-dimethanol

Product 1

HCID 23126022HCID 23126022, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 4.5 g (0.02 mol) 9,9-di(hydroxymethyl)fluorene were added 30 ml tetrahydrofuran, and added 3.3 ml (0.03 mol) pyridine with stirring. To the resulting homogenous mixture was added slowly 2.3 ml (0.02 mol) benzoyl chloride, and the mixture was stirred at temperature for 1 hour, then heated refluxing for 5 hours. Next, the mixture was cooled to room temperature, and 20 ml tetrahydrofuran and 3.3 ml(0.03 mol) pyridine were added with stirring. To the resulting homogenous mixture was slowly added 1.8 ml (0.02 mol) propionyl chloride, and the mixture was stirred at room temperature for 1 hour, and heated refluxing for 5 hours. Then 30 ml water was added to dissolve the resulting salt. The mixture was extracted with toluene. The organic phase was separated, washed with saturated saline for two times, and dried over anhydrous sodium sulfate. The solvent was removed. Recrystallization from ethyl acetate gave 9-(benzoyloxymethyl)-9-(propionyloxymethyl)fluorene as a white crystal, and the yield was 79%. 1HNMR: δ (ppm) 1.23(t, 3H, CH3), 2.39(m, 2H, CH2), 4.48(s, 2H, COOCH2), 4.62(s, 2H, OCH2 linking with benzoyl), 7.33-8.03(m, 13H, ArH)

Workup

  1. stirringthe mixture was stirred at temperature for 1 hour
  2. temperatureheated
  3. temperaturerefluxing for 5 hours
  4. stirringwith stirring
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. temperatureheated
  7. temperaturerefluxing for 5 hours
  8. dissolutionto dissolve the resulting salt
  9. extractionThe mixture was extracted with toluene
  10. customThe organic phase was separated
  11. washwashed with saturated saline for two times
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was removed
  14. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9ecee5bddf50403e821309d6521d6031
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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