p-Anisoyl chloride → HCID 11470410, compound

Participants

Reaction Conditions

Reaction Steps

Anisoyl chloride (17.1 g, 0.1 mol) in THF (100 mL) was added dropwise to a solution of N-isopropylaminoethanol (41.3 g, 0.4 mol) in THF (200 mL) under magnetic stirring at 4 to 10° C. The reaction mixture was stirred for 2 h at room temperature, and the solvent was evaporated in vacuo. The residue was dissolved in ice-cold water (200 mL), and the solution was neutralized with conc. hydrochloric acid. The emulsion was extracted with ethyl acetate (3' 150 mL). Extracts were washed with saturated aqueous NaCl (3' 50 mL), dried over Na2SO4, and evaporated to a solid. Recrystallization from warm toluene-hexanes gave pure 8 as white crystals (20.5 g, 88%). 1H NMR (CDCl3): 7.32 (2H, d, J=8.6 Hz); 6.89 (2H, d, J=8.6 Hz); 4.40 (1H, br. s); 4.09 (1H, m); 3.80 (3H, s); 3.90-3.70 (1H, m); 3.53 (2H, t, J=4.6 Hz); 1.13 (6H, d, J=6.8 Hz). 13C NMR (CDCl3): 173.56 (C=O); 160.60 (C--OMe); 128.71 [C--C(O)]; 128.16 (Arom. CH); 113.89 (Arom. CH); 63.69 (CH2OH); 55.39 (OCH3); 50.60 (N--CH); 44.45 (N--CH2); 21.19 (C--CH3).

Provenance & Evidence