Hydrogen Peroxide → 3-(2-Acetoxymethyl-pyridin-4-yl)-benzoic acid methyl ester

HRID 498240Notes

Reaction equation

HRID 498240 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[CH:11]=2)[CH:5]=1.OO>C(O)(=O)C.C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][O:17][C:3](=[O:2])[CH3:4])[CH:11]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 694891453-(2-Methyl-pyridin-4-yl)-benzoic acid methyl ester

Product 1

HCID 694866013-(2-Acetoxymethyl-pyridin-4-yl)-benzoic acid methyl esterYield 161.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Oxidation of 3-(2-methyl-pyridin-4-yl)-benzoic acid methyl ester (26.2 g, 0.11 mol; example K12) with H2O2 (30%, 31.5 ml, 0.31 mol) in acetic acid (117 ml) at 70° C. for 27 h and subsequent reaction of the N-oxide in acetic acid anhydride (22 ml) at 135° C. for 30 min yielded after aqueous work-up 3-(2-acetoxymethyl-pyridin-4-yl)-benzoic acid methyl ester (25.3 g, 82%) as a brown oil.

Sources & evidence

ORD record
ord-8d92bc8c26f649549c6afb186889ca2c
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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