Iodine → 6-Chloro-3,3-dimethyl-2,3-dihydro-1H-inden-5-ol

Participants

Reaction Conditions

Reaction Steps

81 g of 3,3-dimethyl-5-hydroxy-indane were dissolved in 162 g of glacial acetic acid. After adding a few grains of iodine, 68 g of sulfuryl chloride were added dropwise over the course of about 1 hour at 40°-45° C. The mixture was then warmed to 50° C for 2 hours. The reaction solution was poured into about 1.5 liters of water. The oil which separated out was taken up in chloroform and separated off. The aqueous phase was repeatedly extracted with chloroform. The combined organic phases were washed until neutral, and concentrated. Fractional distillation gave 54 g of 6-chloro-3,3-dimethyl-5-hydroxy-indane; boiling point 134°-36° C/12 mm Hg. ##STR31##

Provenance & Evidence