Iodine → HCID 10954035, compound

Participants

Reaction Conditions

Reaction Steps

Into a three-necks flask equipped with a reflux condenser and a mechanic stirrer, at room temperature and under inert gas, 1,2-dihydronaphthalene (3.9 g; 30 mmoles), sodium nitrite (6.2 g; 90 mmoles) and isopropyl acetate (40 ml) were charged. The mixture was kept under stirring and heated at 50° C. Iodine (3:8 g; 15 mmoles) and then, through a rubber separator, a solution of peracetic acid in acetic acid (8.5 ml—solution 39% w/w) were added in 4 hours. At the end of the addition, the mixture was kept under stirring for further 30 minutes, cooled to 20° C., then a freshly prepared 10% sodium metabisulphite solution was slowly (15 minutes) added up to decoloration of iodine (about 30 ml). The phases were separated and the aqueous phase was washed with isopropyl acetate (2×10 ml). The collected organic phases were washed with a saturated sodium chloride aqueous solution (10 ml). After separation of the phases, the organic phase was dried on sodium sulphate, filtered and the solvent was removed under reduced pressure obtaining crude 2-nitro-3,4dihydronaphthalene (4.7 g; 73% yield) as a brown oil.

Provenance & Evidence