Methyl 3-(benzyloxy)-5-(1-methoxypropan-2-yloxy)benzoate → Methyl 3-hydroxy-5-(1-methoxypropan-2-yloxy)benzoate

HRID 2098328Notes

Reaction equation

HRID 2098328 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH:20]([CH3:24])[CH2:21][O:22][CH3:23])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][CH:20]([CH3:24])[CH2:21][O:22][CH3:23])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 1

HCID 67487869Methyl 3-(benzyloxy)-5-(1-methoxypropan-2-yloxy)benzoate2×

Product 1

HCID 67274118Methyl 3-hydroxy-5-(1-methoxypropan-2-yloxy)benzoateYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Methyl 3-(benzyloxy)-5-(1-methoxypropan-2-yloxy)benzoate (Intermediate 4) (11.2 g, 33.93 mmol) in methanol (150 mL) was added Pd/C (1.12°g, 10% w/w), and the resulting suspension was stirred at ambient temperature overnight under hydrogen atmosphere. The catalyst was filtered off and washed with methanol and THF, and filtrate was evaporated to give methyl 3-hydroxy-5-(1-methoxypropan-2-yloxy)benzoate (8 g, 33.33 mmol, 98%) as white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol and THF, and filtrate
  3. customwas evaporated

Sources & evidence

ORD record
ord-9c3225976c34446db82847029adb45a1
Source dataset
uspto-grants-2013_05
Patent number
US08450494B2

Reaction notes

Loading…