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

HRID 1958774Notes

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]>CC(O)=O.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 AcOH (50 mL) was treated with MnO2 (3.9 g, 45.4 mmol) and the resulting mixture was stirred at 80° C. for 4 h. The mixture was filtered and the filtrate was concentrated. The crude product was purified by CC eluting with DCM to give 3-(2-ethyl-4-formyl-6-methyl-phenyl)-propionic acid as a beige solid (1.76 g). LC-MS: tR=0.86 min.

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
customThe crude product was purified by CC
washeluting with DCM

Sources & evidence

ORD record: ord-6ef2efcd4888436194cc11f8590b80ac
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410151B2

Reaction notes

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