Phenol → 2-(4-Ethylbenzyl)phenol

Reaction equation

[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1)[CH3:11]>C1(C)C=CC=CC=1>[CH2:10]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[OH:9])=[CH:14][CH:13]=1)[CH3:11]

Participants

Procedure

A 60% dispersion of NaH/mineral oil (144 mg, 3.6 mmol) under Ar was added dropwise to a stirred solution of phenol (284 mg, 3 mmol) in PhMe (15 mL). After 10 min, p-ethylbenzyl chloride (1.23 g, 5.3 mmol) in PhMe (2 mL) was added prior to heating the reaction for 6 hr at 80°. After cooling, the volatiles were removed using a rotary evaporator and the residue dissolved in 15 mL of MeOH. The MeOH solution was extracted 4× with hexane prior to concentration. The resulting residue was dissolved in 1:1 EtOAc/H2O (100 mL), the pH adjusted to 5 and the two phases separated. After drying over Na2SO4 and removal of the EtOAc, 390 mg of crude title 2-(4′-ethylbenzyl)phenol was obtained. Prep HPLC yielded 275 mg of clean 2-(4′-ethylbenzyl)phenol.