Sodium Hydroxide → 2-(3,5-Dihydroxy-phenyl)-4-methyl-pentanoic acid methyl ester

HRID 426355Notes

Reaction equation

HRID 426355 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[CH:12]=[C:11]([O:23]CC2C=CC=CC=2)[CH:10]=1)[CH2:5][C:6]([CH3:8])=[CH2:7].[OH-].[Na+]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]([OH:23])[CH:10]=1)[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 577550392-(3,5-Bis-benzyloxyphenyl)-4-methyl-pent-4-enoic acid methyl ester

Product 1

HCID 590047662-(3,5-Dihydroxy-phenyl)-4-methyl-pentanoic acid methyl esterYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (Aldrich cat no 205699, 214 mg) was added to a stirred solution of 2-(3,5-bis-benzyloxyphenyl)-4-methyl-pent-4-enoic acid methyl ester (2.14 g, 5.1 mmol) and NaOH (225 mg, 5.6 mmol) in MeOH (30 mL) at room temperature. Stirring was continued for 2 h under H2 (1 atm.) then the mixture was filtered through Celite, concentrated in vacuo, suspended in water (15 mL) and adjusted to pH 2 with 1M HCl. The mixture was extracted with DCM (3×60 mL); the combined organic layer washed with brine (20 mL), dried (MgSO4), concentrated in vacuo and purified by flash chromatography (silica, 0-20% EtOAc in petroleum ether) to give the title product as a white syrup (1.1 g, 90%).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. extractionThe mixture was extracted with DCM (3×60 mL)
  4. washthe combined organic layer washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (silica, 0-20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-3ae43e72c1dc42c3b87e4e94eb6010f3
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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