Methyl 2,2-dimethyl-3-(3-benzyloxyphenyl)propionate → Methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate

HRID 902713Notes

Reaction equation

HRID 902713 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]CC2C=CC=CC=2)[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4]>CO.Cl.[Pd]>[CH3:1][C:2]([CH3:22])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 1

HCID 68861760Methyl 2,2-dimethyl-3-(3-benzyloxyphenyl)propionate

Product 1

HCID 67520417Methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionateYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of methyl 2,2-dimethyl-3-(3-benzyloxyphenyl)propionate (208 mg, 0.7 mmole) in 10 mL of MeOH and 1 mL of 1N HCl was treated with 10% Pd/C (100 mg) and hydrogenated on a Parr shaker with 50 psi H2 pressure for 1 hour. The catalyst was filtered, and the filtrate was concentrated, diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried and the solvent removed, and gave the titled product, 140 mg (97% yield). MS (ESI) 209 (MH+).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated
  3. additiondiluted with H2O
  4. extractionextracted with Et2O
  5. washThe extracts were washed with H2O
  6. customdried
  7. customthe solvent removed

Sources & evidence

ORD record
ord-a31754affbd64525b13ed67adb06ac19
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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