(3,5-Diethoxy-4-fluorophenyl)methanol → 3,5-Diethoxy-4-fluoro-benzaldehyde

HRID 2264480Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (3,5-diethoxy-4-fluoro-phenyl)-methanol (2.30 g, 10.7 mmol, 1.0 equiv) in 1,2-dichloroethane (50 mL) was added activated MnO2 (2.89 g, 33.3 mmol, 3.1 equiv). The reaction mixture was stirred for 21 h at 50° C. and then filtered through Hyflo Super Cel providing after evaporation of the solvent under reduced pressure 1.90 g (83%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.38 (t, J=7.0 Hz, 6H), 4.09 (q, J=7.0 Hz, 4H). 7.04 (d, J=7.2 Hz, 2H), 9.75 (s, 1H). MS (EI): 212.1 [M]+.

Workup

filtrationfiltered through Hyflo Super Cel
customproviding
customafter evaporation of the solvent under reduced pressure 1.90 g (83%) of the title compound

Sources & evidence

ORD record: ord-820d452d6b254fe1bd2fa1b71902cf08
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855194B2

Reaction notes

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