(S)-2-methyl-1-butyl 4-benzyloxy-4'-biphenylcarboxylate → 4'-[(S)-2-methylbutoxycarbonyl]biphenyl-4-ol

HRID 654421Notes

Reaction equation

HRID 654421 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][C@@H:25]([CH3:28])[CH2:26][CH3:27])=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][C@@H:25]([CH3:28])[CH2:26][CH3:27])=[O:22])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 54320316(S)-2-methyl-1-butyl 4-benzyloxy-4'-biphenylcarboxylate

Product 1

HCID 139075384'-[(S)-2-methylbutoxycarbonyl]biphenyl-4-olYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a 125 ml Parr bomb equipped with a magnetic stirrer were placed 960 mg (S)-2-methyl-1-butyl 4-benzyloxy-4'-biphenylcarboxylate, 200 mg 5% palladium on carbon, and 50 ml ethyl acetate. The bomb was purged with argon and pressurized with 500 psi hydrogen. After stirring at room temperature for one day, thin-layer-chromatographic analysis showed that considerable starting material remained. An additional 200 mg 5% palladium on carbon was carefully added, and the bomb was re-pressurized with 500 psi hydrogen. After stirring for one more day, TLC analysis showed that the reaction was complete. The reaction mixture was filtered through Celite and the solids were washed thoroughly with ethyl acetate. Evaporation of the solvent yielded white crystals which were recrystallized from hexanes at low temperature to yield 0.62 g (85%) of product, mp 111.5°-113° C., whose structure was confirmed by infrared, nuclear magnetic resonance, and mass spectral anaylses, as follows. ##STR38##

Workup

  1. customIn a 125 ml Parr bomb equipped with a magnetic stirrer
  2. customThe bomb was purged with argon
  3. additionAn additional 200 mg 5% palladium on carbon was carefully added
  4. stirringAfter stirring for one more day, TLC analysis
  5. filtrationThe reaction mixture was filtered through Celite
  6. washthe solids were washed thoroughly with ethyl acetate
  7. customEvaporation of the solvent
  8. customyielded white crystals which
  9. customwere recrystallized from hexanes at low temperature

Sources & evidence

ORD record
ord-174b46a8e6534c79b05764d01376e57b
Source dataset
uspto-grants-1992_07
Patent number
US05132041

Reaction notes

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