3-(2-Ethyl-4-hydroxymethyl-6-methyl-phenyl)propionic acid → 3-(2-Ethyl-4-formyl-6-methylphenyl)propionic acid

HRID 1676125Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[C:5]([CH3:11])[C:4]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH3:2]>C(O)(=O)C.O=[Mn]=O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[C:5]([CH3:11])[C:4]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3-(2-ethyl-4-hydroxymethyl-6-methyl-phenyl)-propionic acid (2.8 g, 12.6 mmol) in acetic acid (50 mL) is treated with MnO2 (3.9 g, 45.4 mmol) and the resulting mixture is stirred at 80° C. for 4 h. The mixture is filtered and the filtrate is concentrated. The crude product is purified by CC on silica gel eluting with DCM to give 3-(2-ethyl-4-formyl-6-methyl-phenyl)-propionic acid (1.76 g) as a beige solid; LC-MS: tR=0.86 min.

Workup

filtrationThe mixture is filtered
concentrationthe filtrate is concentrated
customThe crude product is purified by CC on silica gel eluting with DCM

Sources & evidence

ORD record: ord-ba0fbd329eb744328f80fd543fbe243f
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003800B2

Reaction notes

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