4-Methoxyphenol synthesis
- Product Name:4-Methoxyphenol
- CAS Number:150-76-5
- Molecular formula:C7H8O2
- Molecular Weight:124.14
p-Anisaldehyde (50 mmol) is dissolved in CH2Cl2 (100mL) and (o-NO2PhSe)2 (2 mmol) and 30% H2O2 (13mL, 128 mmol) are added. The mixture is stirred magnetically at room temperature (water bath) for 30 minutes. Insoluble catalyst is removed by filtration and washed with CH2Cl2 (20mL) and water (20mL). It can be reused after drying. To the filtrate and washings, water (100mL) is added, and the layers are separated after shaking. The organic layer is washed subsequently with 10% NaHSO3 (100mL), 10% Na2CO3 (100mL), water (100mL) and dried over Na2SO4. 4-methoxyphenol is obtained by alkaline hydrolysis of the residue. Yield: 93%.
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Yield:150-76-5 98%
Reaction Conditions:
with lithium hydroxide monohydrate;ethylene glycol;potassium hydroxide;copper chloride (II) in dimethyl sulfoxide at 120; for 24 h;Inert atmosphere;Reagent/catalyst;Temperature;
Steps:
General Procedure A.
To a test tube containing a magnetic bar was added aryl halide (1.0 mmol), CuCl2 (13.4 mg, 0.1 mmol), KOH (336 mg, 6.0 mmol), ethylene glycol(12 μL, 0.2 mmol), and DMSO/H2O (1.0 mL/0.5 mL). After flushing with argon, the mixture was stirred in a preheated oil bath at 120 °C for 24 h. After cooled to ambient temperature, the reaction mixture was distributed in aqueous HCl (5 %) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under vacuum. The crude product was further purified by column chromatography (EtOAc/n-Hexane) to provide the phenols.
References:
Kim, Jihye;Battsengel, Oyunsaikhan;Liu, Yajun;Chae, Junghyun [Bulletin of the Korean Chemical Society,2015,vol. 36,# 12,p. 2833 - 2840] Location in patent:supporting information
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