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

HRID 33413

Reaction equation

HRID 33413 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) of 9-hydroxy-9-fluorenecarboxylic acid are dissolved in 500 mL of methanol, combined with 5 mL (0.089 mol) of concentrated sulfuric acid and refluxed for 1 hour. After cooling, 100 mL of sodium hydrogen carbonate solution (about pH 8) are added and the methanol is largely evaporated down. The mixture is extracted with dichloromethane and water, the organic phase is dried and evaporated to dryness. The product is purified by recrystallization from ethyl acetate. Yield: 50.0 g of white crystals (93% of theoretical yield).

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe methanol is largely evaporated down
  4. extractionThe mixture is extracted with dichloromethane and water
  5. customthe organic phase is dried
  6. customevaporated to dryness
  7. customThe product is purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-4574abed5e3f4c42926a5f9dfb8c0947
Source dataset
uspto-grants-2008_09
Patent number
US07429600B2

Linked notes

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