Sodium Hydroxide → 4-Methylbenzaldehyde

Participants

Reaction Steps

To a 50 mL flask containing a stirred solution of N-[3-(4-methyl-benzoyl)-5,6,7,8-tetrahydro-naphthalen-2-yl]-benzamide (191 mg, 517 μmol) in tetrahydrofuran (5 mL), ethanol (5 mL) and water (1 mL) under nitrogen was added sodium hydroxide (340 mg, 8.5 mmol) and heated at reflux overnight. Heating was discontinued and solvents removed in vacuo. Added water (20 mL) and extracted with ethyl acetate (3×20 mL). Combined organics were dried with magnesium sulphate and evaporated in vacuo to give 3-amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-p-tolyl-methanone as a partially crystalline red oil 146 mg (107% Yield). LCMS (5 min acidic) 2.99 min 100% pure by ELSD and UV ES+ and AP+ 266. HNMR (CDCl3) >90% pure 7.57-7.55 (m, 2H), 7.27-7.24 (m, 2H), 7.16 (s, 1H), 6.46 (s, 1H), 5.63 (br-s, 2H), 2.72-2.69 (m, 2H), 2.59-2.56 (m, 2H), 2.43 (s, 3H), 1.77-1.73 (m, 4H).

Provenance & Evidence