Tetrahydrofuran → 9-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carboxylic acid

HRID 1799025Notes

Reaction equation

HRID 1799025 reaction equation
[OH:1][C:2]1([C:20]([F:23])([F:22])[F:21])[C:14]2[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[CH:11]=[C:10]([CH3:19])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.O1CCCC1.[OH-].[Na+]>CO>[OH:1][C:2]1([C:20]([F:21])([F:22])[F:23])[C:14]2[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=[C:10]([CH3:19])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59492634methyl 9-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carboxylate

Product 1

HCID 594925279-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carboxylic acidYield 110.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 9-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carboxylate (1.000 g), tetrahydrofuran (4 ml), methanol (6 ml) and 4N aqueous sodium hydroxide solution (1.6 ml) was stirred with heating under reflux for 3 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. Water (30 ml) was added to the obtained residue, and the mixture was adjusted to pH 1 with 6N hydrochloric acid (2 ml), and extracted with ethyl acetate (30 ml). The organic layer was successively washed with water and saturated brine. After addition of anhydrous magnesium sulfate and activated carbon (0.2 g), the mixture was stirred at room temperature for 10 min. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (1.053 g). The residue was directly used for the next reaction without further purification.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. concentrationconcentrated under reduced pressure
  4. additionWater (30 ml) was added to the obtained residue
  5. extractionextracted with ethyl acetate (30 ml)
  6. washThe organic layer was successively washed with water and saturated brine
  7. additionAfter addition of anhydrous magnesium sulfate and activated carbon (0.2 g)
  8. stirringthe mixture was stirred at room temperature for 10 min
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cc3f721ff5bc406396221068c29e521d
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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