Hydrochloric Acid → 7-Octyl-2-fluorenecarboxylic acid

HRID 249215Notes

Reaction equation

HRID 249215 reaction equation
[OH-:1].[Na+].Br[O-].[Na+].[C:6]([C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][C:15]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:16][CH:17]=3)[CH2:12][C:11]=2[CH:10]=1)(=[O:8])C.Cl>O.BrBr.O1CCOCC1>[CH2:22]([C:15]1[CH:14]=[C:13]2[C:18]([C:19]3[CH:20]=[CH:21][C:9]([C:6]([OH:1])=[O:8])=[CH:10][C:11]=3[CH2:12]2)=[CH:17][CH:16]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 197606642-Acetyl-7-octylfluoreneHCID 23673712Sodium hypobromite2×

Product 1

HCID 197606567-Octyl-2-fluorenecarboxylic acidYield 79.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 24408BromineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1.30 g (32.5 mM) of sodium hydroxide in 8.8 ml of water, 0.54 ml (10.5 mM) of bromine was added dropwise at -2° to -0.5° C. under cooling on an ice-common salt bath. After the addition, 3.4 ml of dioxane was added to the mixture to prepare a sodium hypobromite solution. The sodium hypobromite solution was added dropwise to a solution of 1.00 g (3.12 mM) of 2-acetyl-7-octylfluorene in a mixture solvent of 28 ml of dioxane and 2 ml of water at about 5.5° C. under cooling on an ice bath. After the addition, the ice bath was removed and 10 ml of dioxane was added to the resultant mixture, followed by stirring for 1 hour and 50 minutes. After the reaction, the reaction mixture was poured into 200 ml of ice water and acidified with 2.3 ml of hydrochloric acid so as to indicate pH=1 to precipitate a crystal. The crystal was recovered by filtration and recrystallized from acetone to obtain 0.80 g of 7-octyl-2-fluorenecarboxylic acid (Yield: 79.5%).

Workup

  1. temperatureunder cooling on an ice-common salt bath
  2. additionwas added to the mixture
  3. temperatureunder cooling on an ice bath
  4. additionAfter the addition
  5. customthe ice bath was removed
  6. addition10 ml of dioxane was added to the resultant mixture
  7. customAfter the reaction
  8. customto precipitate a crystal
  9. filtrationThe crystal was recovered by filtration
  10. customrecrystallized from acetone

Sources & evidence

ORD record
ord-7af9c6555a4849b483bcd5c889b2e8d3
Source dataset
uspto-grants-1993_05
Patent number
US05213709

Reaction notes

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