Hydrochloric Acid → 3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Participants

Reaction Steps

To a solution of 2-bromophenol (10 g, 57.8 mmol) and 2,5-dichloro-dimethyl hexane (13.04 g, 69.36 mmol) in 160 mL anhydrous CH2Cl2 at 5° C. was added, portionwise, AlCl3 (2.31 g, 17.34 mmol). Upon addition of AlCl3, HCl gas evolution was observed. The solution changed from yellow to reddish orange. The reaction solution was kept at 5-20° C. for two hours and then allowed to stir at room temperature overnight. The reaction mixture was poured into 160 g of ice and extracted with 160 mL CHCl3). The organic phase was washed with water, aqueous, saturated NaHCO3, saturated NaCl and dried (Na2SO4). The organic solution was then concentrated in vacuo and chromatographed (5 to 10% EtOAc/hexane) to provide 12.83 g of 2-bromo-3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene as a white solid in 80% yield. 1H NMR (400 MHz, CDCl3) δ 7.34(s, 1H, aromatic), 6.93(s, 1H, aromatic), 5.24(s, 1H, phenolic OH), 1.64(s; 4H, 2CH2), 1.23(s, 6H, 2CH3), 1.22(s, 6H, 2CH3).

Provenance & Evidence