Hexane → HCID 21927991, compound

HRID 1243346Notes

Reaction equation

HRID 1243346 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:13]([O:15]C)=O)[C:5](=[CH:10][C:11]=1[F:12])[C:6]([O:8]C)=O.[H-].[Na+].[CH3:19]CCCCC.CCCCCC.C(OCC)(=O)C>C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][C:11]=1[F:12])[C:6](=[O:8])[CH2:19][C:13]2=[O:15]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 21927993Dimethyl 4-fluoro-5-methylphthalate

Product 1

HCID 21927991HCID 21927991, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Dimethyl 4-methyl-5-fluorophthalate 9e (1.65 g, 7.29 mmol) was dissolved in anhydrous ethyl acetate (4 mL). Sodium hydride (348 mg, 14.5 mmol) was added and the mixture was heated at 100° C. for 4 hours. The reaction mixture was cooled to room temperature and a mixture containing 10 mL of hexane and 6 mL of ethyl ether/ethanol (1/1) was added. The yellow precepitate was triturated for 5 min, filtered and dried under vacuum. The yellow solid (1.07 g) was then suspended in a solution containing water (22 mL) and concentrated hydrochloric acid (2.2 mL) and the suspension was heated for 17 min at 80° C. The mixture was then lyophilized to give 810 mg (62%) of 5-methyl-6-fluoro-1,3-indandione 9f as a beige solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionwas added
  3. customThe yellow precepitate was triturated for 5 min
  4. filtrationfiltered
  5. customdried under vacuum
  6. additioncontaining water (22 mL) and concentrated hydrochloric acid (2.2 mL)
  7. temperaturethe suspension was heated for 17 min at 80° C

Sources & evidence

ORD record
ord-8f0960b44425487ca056dc3078f88385
Source dataset
uspto-grants-2006_10
Patent number
US07119099B2

Reaction notes

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