3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic Acid Methyl Ester → Methyl 3-(4-formyl-2-methylphenyl)propanoate

HRID 854545Notes

Reaction equation

HRID 854545 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[CH3:14]>C(Cl)(Cl)Cl.O=[Mn]=O>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][C:7]=1[CH3:14]

Participants

4

Reactant 1

HCID 574319763-(4-Hydroxymethyl-2-methyl-phenyl)-propionic Acid Methyl Ester

Product 1

HCID 57431978Methyl 3-(4-formyl-2-methylphenyl)propanoateYield 60%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic acid methyl ester (0.49 g, 2.35 mmol) and MnO2 (0.80 g, 9.20 mmol) in chloroform (5 mL) is stirred at RT for 4 days. The mixture is filtered through Celite; the Celite is washed with copious amounts of EtOAc. The filtrate is concentrated and purified by flash chromatography to yield the title compound (0.29 g, 60%).

Workup

  1. filtrationThe mixture is filtered through Celite
  2. washthe Celite is washed with copious amounts of EtOAc
  3. concentrationThe filtrate is concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-58ca2dc22dcb4ad88f38ca0c681cb6db
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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