3-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid → 3-(4-Formyl-2,6-dimethyl-phenyl)-propionic acid

HRID 1665908Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid (960 mg, 4.6 mmol) in acetic acid (20 mL), MnO2 (1440 mg, 16.6 mmol) is added. The mixture is stirred at 80° C. for 4.5 h before it is filtered. The filtrate is evaporated and the crude product is purified by CC on silica gel eluting with DCM containing 8% of methanol to give 3-(4-formyl-2,6-dimethyl-phenyl)-propionic acid (800 mg) as a beige solid; LC-MS: tR=0.81 min; 1H NMR (D6-DMSO): δ 12.2 (s br, 1H), 9.86 (s, 1H), 7.52 (s, 2H), 2.93-2.85 (m, 2H), 2.38-2.30 (m, 8H).

Workup

filtrationis filtered
customThe filtrate is evaporated
customthe crude product is purified by CC on silica gel eluting with DCM containing 8% of methanol

Sources & evidence

ORD record: ord-87aa9d5368d84544b7ccae9d4074988d
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039644B2

Reaction notes

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