Iodine → 6-Iodochroman-4-ol

Participants

Reaction Steps

To a solution of chroman-4-ol (19.6 g, 131 mmol) in CH2Cl2 (500 mL), at rt., was added HgO (29.7 g, 137 mmol) and I2 (34.8 g, 137 mmol) under N2. After stirring for 48 h. the mixture was filtered through a plug of silica gel and the plug washed plug with 30% EtOAc/Hexanes. The filtrate was washed with 15% Na2S2O3 and the organic layer was dried over Na2CO3; filtered and concentrated in vacuo, yielding 6-iodochroman-4-ol as an off-white solid (32.44 g, 90% crude yield). Recrystallization was performed by dissolving product in hot dichloromethane (250 mL) and slowly adding petroleum ether (250 mL). Overall yield 25.9 g, 72% yield. Anal. Calcd for C9H9IO2; C, 39.16, H, 3.29; found C, 39.26, H, 3.27.

Provenance & Evidence