2,6-Di-tert-butylphenol → HCID 86745643, compound

Participants

Reaction Conditions

Reaction Steps

A dichloromethane (50 mL) solution of 13.6 g (106.5 mmol, 1.1 equiv.) of methyloxalylchloride is added over 15 minutes to a 0° C. stirred slurry of 14.2 g (106.5 mmol, 1.1 equiv.) of AlCl3 in 100 mL of dichloromethane under nitrogen atmosphere. The reaction is stirred at 0° C. for 5 minutes and treated with a dichloromethane (50 mL) solution of 20.0 g (96.9 mmol) of 2,6-di-t-butylphenol over 30 minutes. The reaction is stirred for 3 hours and poured onto 700 mL of ice water and the layers separated. The aqueous layer is extracted with diethyl ether (3×200 mL). The combined organic layers are washed with aqueous 1N HCl (200 mL), water (4×200 mL) and saturated aqueous NaCl, dried over Na2SO4 and concentrated in vacuo to give a yellow solid. Recrystallizing from n-pentane gives a first crop of 8.40 g (mp 85°-86° C.) and a second crop of 4.45 g (mp 82.5°-84° C.). The total yield is 12.85 g (28.33 g theor., 45%).

Provenance & Evidence