(1,1'-Biphenyl)-2-ol → HCID 18786178, compound

Participants

Reaction Conditions

Reaction Steps

At ambient temperature, to a stirred suspension of aluminum chloride (2.0 g, 15.0 mmol) in CH2Cl2 (20 mL) was added 2-phenylphenol (1.28 g, 7.53 mmol). After 30 min, the reaction was cooled to 0° C. To the reaction was added dropwise a solution of 2-chlorobenzoyl chloride (0.94 mL, 7.42 mmol) in CH2Cl2 (20 mL). The reaction was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched into crushed ice (100 g) diluted with sat. aq. KH2PO4 (100 mL) and extracted with CH2Cl2. The organic extracts were dried (Na2SO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with a 3 & 10% EtOAc/pet. ether step gradient to give 0.5g (21%) of the title compound as an off white solid, mp 194-198° C. 1H NMR (DMSO-d6) δ 7.07 (dd, 1H), 7.33 (tt, 1H), 7.40 (tt, 2H), 7.46-7.49 (m, 4H), 7.51-7.59 (m, 4H), 10.8 (s, 1H). mass spectrum (EI) m/z 308 (M+).

Provenance & Evidence