Hexane → HCID 19348715, compound

HRID 1637553Notes

Reaction equation

HRID 1637553 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(C(OCC)=O)[C:14]([O:16]CC)=[O:15].C(OCC)(=O)C.CCCCCC>C(O)C>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19348603HCID 19348603, compound

Product 1

HCID 19348715HCID 19348715, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.0 ml (20.0 mmol) of a 2 N aqueous aqueous solution of sodium hydroxide were added to a solution of 1.30 g (3.55 mmol) of diethyl 2-(2,4-dimethoxyphenyl)-2-pentylmalonate [prepared as described in step (i) above] in 20 ml of ethanol, and the resulting mixture was heated under reflux for 3 hours. At the end of this time, the reaction mixture was freed from ethanol by distillation under reduced pressure, and the resulting residue was acidified with 1 N aqueous hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was disssolved in 20 ml of xylene, and the solution was heated under reflux for 80 minutes. At the end of this time, the reaction mixture was cooled to room temperature, after which it was purified by column chromatography through 50 g of silica gel using a gradient elution method, with mixtures of ethyl acetate and hexane ranging from 1:3 to 1:1 by volume as the eluent, to give 805 mg (yield 85%) of the title carboxylic acid derivative as an oily substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. distillationAt the end of this time, the reaction mixture was freed from ethanol by distillation under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. temperaturethe solution was heated
  9. temperatureunder reflux for 80 minutes
  10. customafter which it was purified by column chromatography through 50 g of silica gel using
  11. washa gradient elution method

Sources & evidence

ORD record
ord-aa08564c44464101ab677fea84370e52
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

Loading…