Hydrochloric Acid → Fluorene

HRID 2229862Notes

Reaction equation

HRID 2229862 reaction equation
C[Al](C)C.Cl.[C:6]1([CH3:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH:10]1[C:11]2[CH2:9][C:8]3[C:12](=[CH:10][CH:11]=[CH:6][CH:7]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 16682925Trimethylaluminum

Product 1

HCID 6853Fluorene

Procedure

About 2 g (0.01 mmol) of 1-carboxylic acid fluorene was suspended in 50 ml of toluene. Then 4.6 ml AlMe3 was added to the solution and the reaction mixture was refluxed for 10 hours. Upon heating, the reaction mixture formed a homogeneous solution. The reaction mixture was cooled to room temperature and then poured into ice cooled diluted aqueous HCl. The organic layer was separated, washed with H2O, and dried over Na2SO4. Then the solvent was removed in vacuo. The colorless residue was extracted with pentane, the solution filtered over silica, and the solvent removed in vacuo. The yield of 1-tert-butyl fluorene, formula 6, was quantitative.

Workup

  1. temperaturethe reaction mixture was refluxed for 10 hours
  2. temperatureUpon heating
  3. customthe reaction mixture formed a homogeneous solution
  4. additionpoured into ice
  5. customThe organic layer was separated
  6. washwashed with H2O
  7. dry with materialdried over Na2SO4
  8. customThen the solvent was removed in vacuo
  9. extractionThe colorless residue was extracted with pentane
  10. filtrationthe solution filtered over silica
  11. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d8449df3b45047ee8213c7f1c4c8d1e9
Source dataset
uspto-grants-2002_07
Patent number
US06420579B1

Reaction notes

Loading…