Sodium Hydroxide → Methyl 2-phenyl-4-methyl-4-pentenoic Acid

HRID 902745Notes

Reaction equation

HRID 902745 reaction equation
[C:1]1([C:7]([CH2:18][C:19]([CH3:21])=[CH2:20])([C:13](OCC)=O)[C:8]([O:10]CC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CCO.O>[CH3:13][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH2:18][C:19]([CH3:21])=[CH2:20])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69251454Diethyl 2-phenyl-2-(2-methyl-2-propenyl)malonate

Product 1

HCID 69253057Methyl 2-phenyl-4-methyl-4-pentenoic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of diethyl 2-phenyl-2-(2-methyl-2-propenyl)malonate (1.63 g, 5.6 mmole) in 20 mL of EtOH and 5 mL of H2O was treated with NaOH (2 g), and refluxed for 3 hours. The reaction was cooled, diluted with H2O, and washed with Et2O. The aqueous layer was acidified and extracted with CH2Cl2. The extracts were dried and evaporated. The residue was dissolved in 5 mL of dimethylacetamide and heated to 125° for 1 hour. The reaction was cooled, diluted with H2O, acified, and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent removed. The residue was dissolved in 10 mL of MEOH, a drop of concentrated H2SO4 was added, and stirred for 24 hours. The reaction was diluted with H2O, and extracted with Et2O. The extracts were washed with H2O, aqueous NaHCO3, dried and the solvent removed, and gave the titled compound, 953 mg (83%). MS (ESI) 205 (MH+)

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction was cooled
  3. washwashed with Et2O
  4. extractionextracted with CH2Cl2
  5. customThe extracts were dried
  6. customevaporated
  7. dissolutionThe residue was dissolved in 5 mL of dimethylacetamide
  8. temperatureheated to 125° for 1 hour
  9. temperatureThe reaction was cooled
  10. additiondiluted with H2O
  11. extractionextracted with Et2O
  12. washThe extracts were washed with H2O
  13. customdried
  14. customthe solvent removed
  15. dissolutionThe residue was dissolved in 10 mL of MEOH
  16. additiona drop of concentrated H2SO4 was added
  17. additionThe reaction was diluted with H2O
  18. extractionextracted with Et2O
  19. washThe extracts were washed with H2O, aqueous NaHCO3
  20. customdried
  21. customthe solvent removed

Sources & evidence

ORD record
ord-9b190725ebbc41608ff7342195b6491d
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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