Methyl 5-acetylsalicylate → JR-13533, Methyl 5-ethyl-2-hydroxybenzoate, 97%

HRID 1902245Notes

Reaction equation

HRID 1902245 reaction equation
[C:1]([C:4]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([OH:14])=[CH:6][CH:5]=1)(=O)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:4]1[CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]([OH:14])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 12101989JR-13533, Methyl 5-ethyl-2-hydroxybenzoate, 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-acetylsalicylate (10.0 g) was hydrogenated in the presence of 5% Pd-C (1.0 g) in ethyl acetate (200 ml) containing 70% HClO4 (2 ml) at room temperature under usual pressure of H2 gas with stirring. The catalyst was filtered off and the filtrate was evaporated in vacuo to give crude methyl 5-ethylsalicylate as pale brown oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c260078bb9544a2e864d771e4ca14b54
Source dataset
uspto-grants-1982_12
Patent number
US04362740

Reaction notes

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