Ethanol → Methyl 9-methylfluorene-9-carboxylate

HRID 33416

Reaction equation

HRID 33416 reaction equation
[Na].[CH2:2]([OH:4])[CH3:3].[CH:5]1[C:17]2C(C(O)=O)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH3:21]I.[CH2:23]([O:25]CC)C>O>[CH3:21][C:3]1([C:2]([O:25][CH3:23])=[O:4])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:17][C:9]=2[C:10]2[C:15]1=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

7

Reactant 5

HCID 702EthanolHCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 748099-CarboxyfluoreneHCID 5360545Sodium

Product 1

HCID 14934655Methyl 9-methylfluorene-9-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

From 7.6 g (0.33 mol) of sodium and 300 mL of ethanol, a sodium ethoxide solution is prepared, to which 69.6 g (0.33 mol) of 9-fluorenecarboxylic acid are added batchwise. After the addition has ended, the mixture is stirred for 2.5 hours at ambient temperature. Then it is evaporated to dryness, the residue is suspended in 600 mL of dimethylformamide, and 93.96 g (0.662 mol) of methyl iodide are added dropwise. The mixture is stirred for 3 hours at constant temperature. The cloudy solution is stirred into 500 mL of water and 300 mL of diethyl ether with cooling and extracted, the organic phase is washed with water and 10% sodium carbonate solution, dried, and evaporated to dryness. The residue is purified by column chromatography, eluent: cyclohexane-ethyl acetate (96:4). Yield: 12.61 g of white crystals (16% of theoretical yield); melting point: 108° C.-109° C.

Workup

  1. additionare added batchwise
  2. additionAfter the addition
  3. customThen it is evaporated to dryness
  4. stirringThe mixture is stirred for 3 hours at constant temperature
  5. temperaturewith cooling
  6. extractionextracted
  7. washthe organic phase is washed with water and 10% sodium carbonate solution
  8. customdried
  9. customevaporated to dryness
  10. customThe residue is purified by column chromatography, eluent

Sources & evidence

ORD record
ord-8d3d2567e946411abba258d8b76140a6
Source dataset
uspto-grants-2008_09
Patent number
US07429600B2

Linked notes

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