3-(4-Benzyloxy-3-methoxyphenyl)-2-methyl-2-phenoxypropionic Acid → 3-(4-Hydroxy-3-methoxy-phenyl)-2-methyl-2-phenoxypropionic Acid

HRID 585196Notes

Reaction equation

HRID 585196 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([CH3:27])([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([OH:19])=[O:18])=[CH:11][C:10]=1[O:28][CH3:29])C1C=CC=CC=1>CCO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([CH3:27])([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:17]([OH:19])=[O:18])=[CH:11][C:10]=1[O:28][CH3:29]

Participants

4

Reactant 1

HCID 223399703-(4-Benzyloxy-3-methoxyphenyl)-2-methyl-2-phenoxypropionic Acid

Product 1

HCID 223399823-(4-Hydroxy-3-methoxy-phenyl)-2-methyl-2-phenoxypropionic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(4-benzyloxy-3-methoxyphenyl)-2-methyl-2-phenoxypropionic acid (6.86 g, 17.5 mmol) in EtOH (175 mL) was added to 5% Pd/C (186 mg, 10 wt %). The mixture was purged first with nitrogen, then with H2, which was then applied at 45 p.s.i. for 2 h. Pd/C was subsequently filtered off through celite, and the filtrate was concentrated to a crude oil (5.42 g, in excess of theory). MS (EI) 301.2 (M−H)−.

Workup

  1. customThe mixture was purged first with nitrogen
  2. filtrationPd/C was subsequently filtered off through celite
  3. concentrationthe filtrate was concentrated to a crude oil (5.42 g, in excess of theory)

Sources & evidence

ORD record
ord-00ea14c959d74cbd8b97b206a88b9394
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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