Science of Synthesis

Wicha, J., Science of Synthesis, (2009) 48, 102.

Reduction of various substrates with zinc in hydrochloric acid is facilitated by adding toluene or another water-immiscible solvent (the Martin modification).[‌16‌,‌39‌] It has been suggested that the presence of the immiscible solvent is beneficial as it keeps undissolved material out of contact with the metal, and because the higher dilution effect limits the side reactions. The indenone derivative ‌7‌ is reduced with zinc dust in a mixture of aqueous hydrochloric acid and toluene to afford the indane ‌8‌ in 75% yield (‌Scheme 10‌).[‌40‌] Analogous reduction reactions can be carried out in a mixture of aqueous hydrochloric acid, ethanol, and benzene.[‌41‌]

‌Meeeee 88‌ Meeeeeeee ee ee Meeeeeee Meeeeeeeee eeee Meee ee Meeeeeeeeeee Meee/Meeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeee-8-eeeeee-8,8-eeeeeee-8M-eeeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee 8,8-eeeeeeeee-8-eeeeee-8,8-eeeeeee-8M-eeeee-8-eee (‌8‌; 88.8 e, 8.888 eee) ee eeeeeee (88 eM) eee eeeee ee e eeeeeeeeee ee eeeeeee eeeeeeeee Me eeee (88.8 e, 8.888 eee) ee M8M (88 eM) eee eeeee ee MMe (88 eM). Mee eeeeeee eee eeeeee eeeee eeeeee eee 88 e, eeee e eeeeee eeeeeee ee eeeee ee MMe (88 eM) eee eeeee, eee eeeeeee eee eeeeeeeee eee 88 e. Meeee eeeeeee, eee eeeeeee eee eeeeee eeee M8M (888 eM) eee eee eeeeeee eee eeeeeeeee eeee Me8M (888 eM). Mee eeeeeee eeeeeee eee eeeeee eeee M8M (888 eM) eee eeeee (88 eM), eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee); eeeee: 88.8 e (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e, 888.
• 8.Meeeee-Meee, (8888) M 8e, 88.
• 8.Meeeee-Meee, (8888) M 8e8, 888.