Sulfuric Acid → HCID 20336687, compound

Participants

Reaction Steps

The sample of (25A) was dissolved in 250 ml of dry acetone and stirred overnight under argon with 25.2 g of sodium iodide and 1.0 g of lithium iodide. The (CHCl3) analysis the next day of the reaction mixture showed little or no reaction had taken place. A 0.25 ml portion of concentrated sulfuric acid was added to the dark colored reaction mixture and it was then heated to reflux using an oil bath. The mixture rapidly became very viscous and the analysis after a few minutes showed considerable amounts of (27A) had formed at the expense of (25A). After 1 hour of reflux the resultant very dark colored reaction mixture was evaporated in vacuo. The residue was mixed with ether and washed with aqueous sodium thiosulfate and then with saturated aqueous sodium bicarbonate. The resultant extract was dried (MgSO4) and evaporated in vacuo. The resultant 27.8 g of residue was distilled in vacuo to yield 18.7 g of (27A) as a yellow oil, bp 78°-88° (0.2 mm); Rf (CHCl3) 0.58; nmr (CDCl3) δ 0.90 (3H, broad t, J=6.0 Hz), 1.14 (6H, s), 1.0-1.8 (6H, m) 7.66 (1H, d, J=14.8 Hz) and 8.07 ppm (1H, d, J=14.8 Hz); ir (film) 940, 1040, 1080, 1470, 1560, 1688, 2860, 2930 and 2960 cm-1.

Provenance & Evidence