3-Methoxyphenol → 4-(3-Methoxyphenoxy)benzaldehyde

HRID 2360354Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of p-fluorobenzaldehyde (1.6 mmol, 0.2 g) in dimethylformamide (8 mLs) was added 3-methoxyphenol (3.52 mmol, 0.437 g) and cesium carbonate (3.52 mmol, 1.15 g). The reaction was heated to 90° C. for 3 hours at which time it was cooled to room temperature and filtered through a fritted funnel. The reaction mixture was diluted with 125 mL of ethyl acetate and extracted with eight 15 mL portions of water and one 10 mL portion of brine. The organic layer was dried with magnesium sulfate and evaporated to dryness. The crude oil was purified by flash chromatography to recover 0.365 g (1.6 mmol) of the title product. 1H NMR (300 MHz, CDCl3) δ 9.92 (s, 1H), 7.84 (d, J=8.7, 2H), 7.29 (dd, J=5.7, 13.9, 1H), 7.07 (d, J=8.7, 2H), 6.76 (d, J=8.3, 1H), 6.72-6.57 (m, 2H), 3.80 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 190.99, 163.25, 161.38, 156.42, 132.15, 130.76, 117.91, 112.63, 110.81, 106.59, 55.66.

Workup

temperaturewas cooled to room temperature
filtrationfiltered through a fritted funnel
additionThe reaction mixture was diluted with 125 mL of ethyl acetate
extractionextracted with eight 15 mL portions of water and one 10 mL portion of brine
dry with materialThe organic layer was dried with magnesium sulfate
customevaporated to dryness
customThe crude oil was purified by flash chromatography

Sources & evidence

ORD record: ord-00bb84e003e449ba937238341536f3b2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686046B2

Reaction notes

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