3-(hexyloxy)benzaldehyde synthesis
- Product Name:3-(hexyloxy)benzaldehyde
- CAS Number:24083-09-8
- Molecular formula:C13H18O2
- Molecular Weight:206.28
Yield:24083-09-8 97%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 80; for 2 h;Inert atmosphere;
Steps:
1 Compound [6]
Compound [6]
Under a nitrogen atmosphere, 3-hydroxybenzaldehyde (4.9 g, 40 mmol), 1-bromohexane (7.3 g, 44 mmol), and potassium carbonate (6.9 g, 50 mmol) were added in 60 mL of dry N,N-dimethylformamide (DMF), and the whole was heated at 80° C. for 2 hours. The reaction solution was allowed to cool to room temperature, then insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue, ethyl acetate and saturated sodium chloride were added. The resultant mixture was subjected to a liquid separation operation, and the organic phase was extracted. The organic phase was washed with saturated sodium chloride. The organic phase was dried over sodium sulfate, then the sodium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, hexane: ethyl acetate=10:0 to 7:3 (v/v)), yielding the target compound: Yield 97%; 1H NMR (500 MHz, CDC3): δ9.97 (s, 1H), 7.46-7.41 (m, 2H), 7.40-6.36 (m, 1H), 7.20-7.14 (m, 1H), 4.01 (t, 2H, J=6.5 Hz), 1.84-1.76 (m, 2H), 1.52-1.43 (m, 2H), 1.40-1.30 (m, 4H), 0.96-0.86 (m, 3H).
References:
US2015/25157,2015,A1 Location in patent:Paragraph 0133; 0134; 0142
