methyl (RS)-5-(3-benzyloxyphenyl)-5-oxo-4-(2-methylphenyl)-pentanoate → methyl (RS)-5-(3-hydroxyphenyl)-5-oxo-4-(2-methylphenyl)pentanoate

HRID 322938Notes

Reaction equation

HRID 322938 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:30])[CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.C(OC)(=O)C.Cl.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:15](=[O:30])[CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 1

HCID 10525154methyl (RS)-5-(3-benzyloxyphenyl)-5-oxo-4-(2-methylphenyl)-pentanoate

Product 1

HCID 10805064methyl (RS)-5-(3-hydroxyphenyl)-5-oxo-4-(2-methylphenyl)pentanoateYield 60.8%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6584Methyl AcetateSolvent

Procedure

A solution of methyl (RS)-5-(3-benzyloxyphenyl)-5-oxo-4-(2-methylphenyl)-pentanoate (46 g) in methanol (250 mL), methyl acetate (250 mL) and concentrated hydrochloric acid (25 mL) is treated with palladium on carbon catalyst (5%; 1.5 g) and shaken under hydrogen at atmospheric pressure and room temperature for 2 hours. The suspension is filtered, and evaporated. The residue is dissolved in ethyl acetate, washed with water, dried and evaporated, and the residue is recrystallised from a mixture of ethyl acetate and cyclohexane, giving methyl (RS)-5-(3-hydroxyphenyl)-5-oxo-4-(2-methylphenyl)pentanoate as colourless crystals (21.7 g), m.p. 101-103° C.

Workup

  1. filtrationThe suspension is filtered
  2. customevaporated
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customthe residue is recrystallised from a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-70cfee85347a4679af038929b16fd78d
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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