Methyl 3-{(1S)-2-methoxy-(1-methylethyl)oxy}-5-{[(2-methylphenyl)methyl]oxy}benzoate → methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

HRID 1510298Notes

Reaction equation

HRID 1510298 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([O:17]CC2C=CC=CC=2C)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])[CH3:5]>C1COCC1.C(O)C.[Pd]>[OH:17][C:15]1[CH:14]=[C:9]([CH:8]=[C:7]([O:6][C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 1

HCID 59127156Methyl 3-{(1S)-2-methoxy-(1-methylethyl)oxy}-5-{[(2-methylphenyl)methyl]oxy}benzoate

Product 1

HCID 59127146methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoateYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Methyl 3-{(1S)-2-methoxy-(1-methylethyl)oxy}-5-{[(2-methylphenyl)methyl]oxy}benzoate (50 g, 0.152 mol) was dissolved in THF/ethanol (1:1, 600 ml) and 10% Palladium on carbon (5.0 g) was added. The mixture was hydrogenated under normal pressure at room temperature. The catalyst was filtered off, and the filtrate concentrated in vacuo to give the desired compound (36.7 g, 99%).

Workup

  1. customwas hydrogenated under normal pressure at room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-77c9f1a0eaeb48bc86d9cab4625d3e3c
Source dataset
uspto-grants-2012_07
Patent number
US08211925B2

Reaction notes

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