Methyl 4-benzyloxy-5-isopropyl-2-methoxybenzoate → Methyl 4-hydroxy-5-isopropyl-2-methoxybenzoate

HRID 389950Notes

Reaction equation

HRID 389950 reaction equation
C([O:8][C:9]1[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:22][CH3:23])[CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:22][CH3:23])[CH:10]=1

Participants

4

Reactant 1

HCID 58236472Methyl 4-benzyloxy-5-isopropyl-2-methoxybenzoate

Product 1

HCID 58236464Methyl 4-hydroxy-5-isopropyl-2-methoxybenzoateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (80 mg) was added to a suspension of methyl 4-benzyloxy-5-isopropyl-2-methoxybenzoate (624 mg, 1.99 mmol) in methanol (16 ml) and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The mixture was filtered, the catalyst was rinsed with methanol (3×5 ml) and the combined filtrates were evaporated in vacuo to afford methyl 4-hydroxy-5-isopropyl-2-methoxybenzoate (432 mg, 97%) as an off-white solid. 1H NMR (DMSO-d6) 10.18 (1H, br s), 7.52 (1H, s), 6.52 (1H, s), 3.73 (3H, s), 3.71 (3H, s), 3.11 (1H, m), 1.14 (6H, d). MS: [M+Na]+ 247.

Workup

  1. filtrationThe mixture was filtered
  2. washthe catalyst was rinsed with methanol (3×5 ml)
  3. customthe combined filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-194cb8af727842e78845819e3133c21e
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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