Ethyl formate → 9-formyl-9H-fluorene-2-carboxylic acid

HRID 2387649Notes

Reaction equation

HRID 2387649 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)([OH:3])=[O:2].C[C:18](C)([O-:20])C.[K+].C(OCC)=O>CN(C)C=O>[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]([CH:18]=[O:20])[C:6]=2[CH:5]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 3485919H-fluorene-2-carboxylic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 592023689-formyl-9H-fluorene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Carboxyfluorene (2.8 g, 0.014 mole) was dissolved in anhydrous dimethylformamide (DMF, 133 mL). Potassium t-butoxide (12.5 g, 0.11 mole) and ethyl formate (400 mL) were added to the reaction solution. The temperature of the solution was increased to 60° C. for 5-10 minutes. The reaction solution was cooled to room temperature. Total reaction time was three hours. Ethyl formate was distilled off and 1M hydrochloric acid (150 mL) was added to the reaction mixture. The solid was filtered and washed with distilled water. The precipitate was dried overnight under reduced pressure with phosphorous pentoxide present. NMR confirmed the structure by the appearance of one new proton at δ11.47 ppm (aldehyde hydrogen).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. distillationEthyl formate was distilled off
  3. addition1M hydrochloric acid (150 mL) was added to the reaction mixture
  4. filtrationThe solid was filtered
  5. washwashed with distilled water
  6. dry with materialThe precipitate was dried overnight under reduced pressure with phosphorous pentoxide present

Sources & evidence

ORD record
ord-3c3df30b11374957bd37b5d428e36ff9
Source dataset
uspto-grants-2012_09
Patent number
US08268948B2

Reaction notes

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