(4-Chloro-3,5-diethoxyphenyl)methanol → 4-Chloro-3,5-diethoxybenzaldehyde

HRID 913115Notes

Reaction equation

HRID 913115 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([CH2:11][OH:12])=[CH:4][C:3]=1[O:13][CH2:14][CH3:15]>C1COCC1.O=[Mn]=O>[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([CH:11]=[O:12])=[CH:4][C:3]=1[O:13][CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 67147397(4-Chloro-3,5-diethoxyphenyl)methanol

Product 1

HCID 592103754-Chloro-3,5-diethoxybenzaldehydeYield 93.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-chloro-3,5-diethoxy-phenyl)-methanol (4.0 g, 17.34 mmol, 1.0 equiv) in THF (40 mL) was added activated MnO2 (15.08 g, 173.4 mmol, 10.0 equiv) and the reaction mixture stirred for 18 h at rt. Filtration through Hyflo Super Cel and purification of the crude material by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate provided 3.7 g (92%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.50 (t, J=7.0 Hz, 6H), 4.19 (q, J=7.0 Hz, 4H), 7.07 (s, 2H), 9.89 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.61, 65.22, 106.26, 118.64, 135.08, 156.22, 191.01. MS (EI): 229.4 [M]+.

Workup

  1. filtrationFiltration
  2. customthrough Hyflo Super Cel and purification of the crude material by silica column chromatography
  3. washeluting with a gradient of heptane/ethyl acetate

Sources & evidence

ORD record
ord-60b9077be7d448fdafdc7b0bfb1343f3
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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