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

HRID 2121493Notes

Reaction equation

HRID 2121493 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>[CH3:23][O:16][C:15]([C:2]1([OH:1])[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)=[O:17]

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 is 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 (approx. pH 8) is added and the methanol is largely evaporated down. It is extracted with dichloromethane and water; the organic phase is dried and evaporated to dryness. The purification is carried out 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. extractionIt is extracted with dichloromethane and water
  5. customthe organic phase is dried
  6. customevaporated to dryness
  7. customThe purification
  8. customis carried out by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d704c7e366284e218a7ca989659a4512
Source dataset
uspto-grants-2004_02
Patent number
US06696462B2

Reaction notes

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