A
500-ml. round-bottomed flask, equipped with a reflux condenser, is charged with
40 g. (0.33 mole) of powdered tin (Note
1) and (Note
2),
52 g. (0.19 mole) of anisoin (Note
3),
52 ml. of concentrated hydrochloric acid (Note
4), and
60 ml. of 95% alcohol. After the mixture is refluxed for 24 hours (Note
5), the boiling solution is decanted from undissolved
tin, cooled to 0°, and the white crystals are filtered by suction. The filtrate is heated to boiling and then used to wash the
tin by decantation. The combined washings are cooled to 0°, and the crystalline solid is collected by suction filtration. Recrystallization of the combined solids from
450 ml. of boiling 95% ethanol (Note
6) and (Note
7) gives, on cooling to 0°, colorless crystals of
deoxyanisoin melting at
108–111°. The yield is
42–45 g. (
86–92%).