HCID 58236461, compound → Methyl 4-hydroxy-5-isopropyl-2-(methoxymethyloxy)benzoate

HRID 389965Notes

Reaction equation

HRID 389965 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][CH2:23][O:24][CH3:25])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[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][CH2:23][O:24][CH3:25])[CH:10]=1

Participants

4

Reactant 1

HCID 58236461HCID 58236461, compound

Product 1

HCID 58236469Methyl 4-hydroxy-5-isopropyl-2-(methoxymethyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The crude methyl 4-benzyloxy-5-isopropyl-2-(methoxymethyloxy)benzoate was dissolved in methanol (20 ml), 10% palladium on carbon (160 mg) was added and the mixture was stirred at room temperature under a hydrogen atmosphere for 16 hours. The mixture was filtered, the catalyst was rinsed with methanol (3×5 ml) and the combined filtrates were evaporated in vacuo to afford crude methyl 4-hydroxy-5-isopropyl-2-(methoxymethyloxy)benzoate as a colourless oily solid that was used in the next step without further purification. 1H NMR (DMSO-d6) 10.19 (1H, br s), 7.52 (1H, s), 6.57 (1H, s), 5.13 (2H, s), 3.73 (3H, s), 3.40 (3H, s), 3.11 (1H, m), 1.13 (6H, d). MS: [M−H]− 253.

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-02012b883239488b987221b0ae1ec968
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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