ChemicalBook CAS DataBase List Monobenzone

Monobenzone synthesis

13synthesis methods

Product Name:Monobenzone
CAS Number:103-16-2
Molecular formula:C13H12O2
Molecular Weight:200.23

4-Benzyloxyphenol Synthesis: Add 2.63g (0.028mol) of hydroquinone to a 100mL conical flask, weigh 1.12g (0.028mol) of sodium hydroxide, add 8mL of water, wait for the sodium hydroxide to dissolve and add dropwise to the conical flask with hydroquinone, shake well, then add 15mL of DMF and 2.52g (0.02mol) of benzyl chloride, under microwave radiation power of 320W The reaction was cooled to room temperature at the end of the reaction. The reaction was first adjusted to alkalinity with 10% sodium hydroxide, filtered, and the filtrate was washed with 10% sodium hydroxide until the filtrate was colorless (the filtrate was hydroquinone bis(benzyl ether), which could be recycled). The filtrate was acidified with hydrochloric acid to make Monobenzone completely precipitated, and then washed by filtration and ice water, recrystallized with alcohol and water, and decolorized by activated carbon to obtain 2.55g of white solid, the yield was 63.79%.

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Yield:103-16-2 95.7%

Reaction Conditions:

with dihydrogen peroxide in dichloromethane;water at 20; for 4 h;Inert atmosphere;Reagent/catalyst;

Steps:

Conversion of the phenylboronic acid 9 to the phenol 10 using hydrogen peroxide (Scheme S2)

A mixture of phenylboronic acid 9 (228 mg, 1.00 mmol) and 30% aqueous hydrogen peroxide solution (0.20 mL, 2.0 mmol) in dichloromethane (1 mL) was stirred under argon at ambient temperature for 4 h. Then, 10% aqueous sodium thiosulfate solution (10 mL) was added, and the mixture was extracted with dichloromethane (3 20 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Column chromatography (chloroform/methanol = 80:1) gave phenol 10 (192 mg, 0.956 mmol, 95.7% yield).

References:

Karaki, Fumika;Kiguchi, Takuto;Itoh, Kennosuke;Sato, Noriko;Konishi, Kazuhide;Fujii, Hideaki [Tetrahedron,2021,vol. 97,art. no. 132411] Location in patent:supporting information