Hydrochloric Acid → 9-methyl-9H-fluorene-2,7-diol

HRID 2416365Notes

Reaction equation

HRID 2416365 reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([O:18]C(=O)C)=[CH:12][CH:13]=3)[CH:8]([CH3:22])[C:7]=2[CH:6]=1)(=O)C.O.[OH-].[Li+].Cl>C(O)CO>[OH:4][C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([OH:18])=[CH:12][CH:13]=3)[CH:8]([CH3:22])[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 226302552,7-Diacetyloxy-9-methylfluorene

Product 1

HCID 219606279-methyl-9H-fluorene-2,7-diolYield 84.2%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 2,7-diacetyloxy-9-methylfluorene (12 g), lithium hydroxide monohydrate (3.42 g) and ethylene glycol (120 mL) was refluxed for one hour by heating. The reaction mixture was poured into 6M-hydrochloric acid and extracted with ethyl acetate. The organic layer was sufficiently washed with water and then dried on anhydrous magnesium sulfate. The solvent was distilled off from this organic layer under reduced pressure to obtain 2,7-dihydroxy-9-methylfluorene (7.24 g) of light brown crystal. Melting point: 191.5-196.3° C.

Workup

  1. temperaturewas refluxed for one hour
  2. temperatureby heating
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was sufficiently washed with water
  5. dry with materialdried on anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off from this organic layer under reduced pressure

Sources & evidence

ORD record
ord-05461abc9eb2475ba7d0a15a35254593
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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