2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 20267188, compound

Participants

Reaction Steps

A mixture of 24 g of methyl 3,4-dihydro-1-methylnaphthalenecarboxylate, 30 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 400 ml of toluene was heated at reflux for 18 hours. The reaction mixture was then filtered and concentrated in vacuo. Sodium bisulfite solution (150 ml, 25%) was added to the residue, followed by 150 ml of toluene and 50 ml of ether. The latter mixture was washed twice with each of the following: 25% sodium bisulfite solution, concentrated sodium chloride solution, sodium bicarbonate solution and water. The organic solution was dried over anhydrous sodium sulfate and concentrated in vacuo to give 17.5 g of methyl 1-methylnaphthalenecarboxylate as an oil, which upon further purification gave the product in crystalline form, m.p. 48°-49° C.

Provenance & Evidence