Nitrogen → 2-(Naphthalen-1-yl)acetyl chloride

Participants

Reaction Conditions

Reaction Steps

1-Naphthylacetylchloride was synthesized from 1-naphthylacetic acid (20.0 g, 107.4 mmol) which was dissolved in CH2Cl2 (200 mL) and the solution was cooled to 0° C. Oxalylchloride (11.20 mL, 128.90 mmol) was added to the solution dropwise over 20 min. under the atmosphere of N2 then followed by one drop of DMF. The mixture was then allowed to warm to room temperature where it was stirred for 12 hours. The reaction mixture was concentrated under vacuum, the resulting residue was redissolved in CH2Cl2 (200 mL) and the solvents were evaporated in vacuo to give 1-naphthylacetylchloride 21.90 g (99%) as a dark oil: 1H-NMR (400 MHz, CDCl3) δ 7.92-7.84 (m, 3H), 7.61-7.42 (m, 4H), 4.58 (s, 2H).

Provenance & Evidence