ChemicalBook CAS DataBase List 3-Methoxyphenol

3-Methoxyphenol synthesis

12synthesis methods

Product Name:3-Methoxyphenol
CAS Number:150-19-6
Molecular formula:C7H8O2
Molecular Weight:124.14

synthesis of 3-methoxyphenol: The 1 mole of resorcinol is treated rapidly with stirring, in a three-necked flask provided with a reflux condenser, stirrer, internal thermometer, and dropping funnel, with 1.25 mole of 10% sodium hydroxide. With vigorous stirring, 1 mole of dimethyl sulfate is added in such a way that the temperature remains below 40° C (water cooling). To complete the reaction and to destroy unchanged dimethyl sulfate, the mixture is then heated for 30 min on a boiling water bath. After cooling, the organic layer is separated off and the aqueous solution is extracted several times with ether. The combined organic phases are washed with dilute sodium carbonate and then with water, dried with calcium chloride, and fractionated. Unchanged resorcinol can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 3-methoxyphenol is 50%, b.p. 113-115 °C/5 mm; b.p. 144°C/25mm; n20/D 1.552; d=1.131 g/mL at 25 °C.
Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 206-207, (1973)

10365-98-7 Synthesis

10365-98-7
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$9.00/10g

150-19-6
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$6.00/5g

Yield:150-19-6 99%

Reaction Conditions:

with dihydrogen peroxide in ethanol at 20; for 0.0166667 h;Green chemistry;Solvent;

Steps:

General procedure for the oxidation using H2O2

General procedure: A 25 ml flask was charged with phenylboronic acid (1 mmol). Then 1.6 mL H2O2 and 1 mL EtOH were added under stirring. The reaction was stirred for 1 min, then quenched by water (10 ml). The aqueous layer was extracted with 20 mL ethyl acetate for three times. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The pure product was obtained without flash column chromatography and the purity was determine by TLC.

References:

Dong, Zhenhua;Liu, Mengmeng;Pan, Hongguo [Arkivoc,2021,vol. 2021,# 8]