4-Hydroxy-2-methoxybenzaldehyde synthesis
- Product Name:4-Hydroxy-2-methoxybenzaldehyde
- CAS Number:18278-34-7
- Molecular formula:C8H8O3
- Molecular Weight:152.15
114628-32-9
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18278-34-7
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Yield:18278-34-7 88.2%
Reaction Conditions:
with hydrogenchloride;water in methanol at 20;
Steps:
Synthesis of 5-bromo-4-hydroxy-2-methoxybenzaldehyde (4b)
General procedure: A solution of 5-bromo-2-hydroxy-4-(methoxymethoxy)benzaldehyde (3b) (5g, 19.2mmol) in dry acetone (30mL)was added K2CO3(8 g, 57.6mmol) portionwise, followed by MeI (1.31 mL, 21.1 mmol) at room temperature. After 16 h, the reaction mixture was then filtered and the filtercake was washed with acetone (50 mL). The filtrate was concentrated under reduced pressure and the residue was dissolved in EtOAc (30 mL), washed with water (30 mL) and brine (30 mL). The organic layer was dried over MgSO4 ,and filtered and the filtrate was concentrated in vacuo to give 5-bromo-2-methoxy-4-(methoxymethoxy) benzaldehyde (5.26 g, 100 %) as a white crystalline solid. mp: 71-73°C. To a solution of 5-bromo-2-methoxy-4-(methoxymethoxy) benzaldehyde(5.26 g, 19.2 mmol) in MeOH (250 mL) was added 6N-HCl (150 mL) and the mixture was stirred for 3-5 h at room temperature. The resulting reaction mixture was quenched with H2O (150 mL) and extracted with EtOAc (3×150 mL). The combined organic layers were washed with saturated NaHCO3 (200 mL) solution and dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was further purified by flash column chromatography on silica gel to afford 5-bromo-4-hydroxy-2- methoxybenzaldehyde (4.19 g, 95 %).
References:
Wang, Zengtao;Liu, Zhiguo;Lee, Woojung;Kim, Su-Nam;Yoon, Goo;Cheon, Seung Hoon [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 15,p. 3337 - 3340] Location in patent:supporting information
150-19-6
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673-22-3
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700-44-7
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18278-34-7
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$16.00/250mg
403477-22-5
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18278-34-7
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150-19-6
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18278-34-7
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67395-05-5
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18278-34-7
246 suppliers
$16.00/250mg