3-DIMETHYLAMINOMETHYL-4-HYDROXY-BENZALDEHYDE synthesis
- Product Name:3-DIMETHYLAMINOMETHYL-4-HYDROXY-BENZALDEHYDE
- CAS Number:116546-04-4
- Molecular formula:C10H13NO2
- Molecular Weight:179.22
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Yield: 39%
Reaction Conditions:
in methanol;water at 50;
Steps:
3-((dimethylamino)methyl)-4-hydroxybenzaldehyde (4)
A mixture of 4-hydroxybenzaldehyde (10.0 g, 80 mmol), 33% aqueous dimethylamine (11.0 g, 80 mmol) and 35% formaldehyde solution (8.0 g, 95 mmol) in 80 mL methanol was stirred overnight at 50oC. After removal of methaol under reduced pressure the resedue was extracted with EtOAc (15 mL×3). The organic phase was was dried by anhydrous sodium sulfate, filtrated and concentrated under reduced pressure. The obtained oil-like mixture was purified by column chromatography (EtOAc/petroether 1:10 v/v) to give 4 as a yellow solid (14.34 g,39%): mp: 80-81oC; 1H NMR (500MHz, CDCl3): δ=2.36 (s, 6H, N(CH3)2), 3.73 (s, 1H, CH2), 6.92-6.90 (d, J= 8.35Hz, 1H, arom), 7.55-7.54 (d, J= 2.1Hz, 1H, arom), 7.71 (dd, J= 8.35Hz, 2.1Hz, 1H, arom), 8.61 (s, 1H, OH), 9.81 ppm (s, 1H, CHO); IR (KBr): ṽ = 3421, 2957, 2863, 2729, 1684, 1595, 1494 cm-1.
References:
Fang, Xubin;Fang, Lei;Gou, Shaohua;Cheng, Lin [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 5,p. 1297 - 1301] Location in patent:supporting information
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116546-04-4
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