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ChemicalBook CAS DataBase List 2-BENZYL-4-METHYLPHENOL
716-96-1

2-BENZYL-4-METHYLPHENOL synthesis

13synthesis methods
-

Yield:716-96-1 50% ,6627-39-0 5% ,834-25-3 2%

Reaction Conditions:

Stage #1: p-cresolwith n-butyllithium in toluene; for 0.25 h;Inert atmosphere;
Stage #2: benzyl bromide in toluene at 80;Inert atmosphere;

Steps:

4.2. General procedure B (GPB) for the dearomatization reaction in non-aqueous conditions

General procedure: To solution of phenol (1 mmol) in a solvent under argon atmosphere n-BuLi (2.7 M in toluene; 0.82 mL; 2.2 mmol) was added dropwise. After addition of the additives BnBr (1.2 mmol) was applied. The reaction mixture was warmed up to 80 °C and stirred at this temperature overnight. After cooling water was added and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with brine and dried with phase separator or on MgSO4. The crude product solution was filtered if necessary, and then solvent was removed with rotary evaporator.The products were separated by flash chromatography on silica gel (petroleum ether/EtOAc).

References:

Lopu?anskaja, Eleana;Kooli, Anni;Paju, Anne;J?rving, Ivar;Lopp, Margus [Tetrahedron,2021,vol. 83]

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