Sulfuric Acid → Methyl 9-hydroxy-9H-fluorene-9-carboxylate

HRID 10367

Reaction equation

HRID 10367 reaction equation
[OH:1][C:2]1([C:15]([OH:17])=[O:16])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.S(=O)(=O)(O)O.[C:23](=O)([O-])O.[Na+]>CO>[OH:1][C:2]1([C:15]([O:17][CH3:23])=[O:16])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]2[C:14]1=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10087FlurenolHCID 516892Sodium Bicarbonate

Product 1

HCID 267210Methyl 9-hydroxy-9H-fluorene-9-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50.4 g (0.223 mol) 9-hydroxy-9-fluorenecarboxylic acid are dissolved in 500 ml of methanol, combined with 5 ml (0.089 mol) conc. sulphuric acid and refluxed for 1 hour. After cooling 100 ml sodium hydrogen carbonate solution (about pH 8) are added, and the methanol is largely distilled off under reduced pressure. The residue remaining is extracted with dichloromethane and water, the organic phase is dried and evaporated to dryness.

Workup

  1. temperaturerefluxed for 1 hour
  2. additionare added
  3. distillationthe methanol is largely distilled off under reduced pressure
  4. extractionThe residue remaining is extracted with dichloromethane and water
  5. customthe organic phase is dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-15d92f3715f741f0bf46d9dec45f38a3
Source dataset
uspto-grants-2006_08
Patent number
US07094788B2

Linked notes

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