Sodium Hydroxide → 4-Methyl-2-phenylpentanoic acid

HRID 902746Notes

Reaction equation

HRID 902746 reaction equation
C[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH2:6][C:7]([CH3:9])=[CH2:8])[C:3]([OH:5])=[O:4].[OH-].[Na+]>O>[C:10]1([CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69253057Methyl 2-phenyl-4-methyl-4-pentenoic Acid

Product 1

HCID 2365774-Methyl-2-phenylpentanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 2-phenyl-4-methyl-4-pentenoic acid (850 mg, 4.15 mmole) in 10 mL of MeOHwas treated with 5 mL of 2.5N NaOH and heated to 50° for 30 minutes. The reaction was cooled, diluted with H2O and washed with Et2O. The aqueous phase was acified, and extracted with CH2Cl2. The extracts were washed with H2O, dried and the solvent removed. The residue was dissolved in 25 mL of EtOAc, and hydrogenated over a 10% Pd/C catalyst, at 1 atmosphere H2 pressure, for 2 hours. The catalyst was filtered and the solvent removed and gave the titled compound, 647 mg (81%). MS (ESI) 193 (MH+)

Workup

  1. temperatureheated to 50° for 30 minutes
  2. temperatureThe reaction was cooled
  3. washwashed with Et2O
  4. extractionextracted with CH2Cl2
  5. washThe extracts were washed with H2O
  6. customdried
  7. customthe solvent removed
  8. dissolutionThe residue was dissolved in 25 mL of EtOAc
  9. filtrationThe catalyst was filtered
  10. customthe solvent removed

Sources & evidence

ORD record
ord-963f3a8ff95a4f48950097331f079fa7
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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