Science of Synthesis

Wicha, J., Science of Synthesis, (2009) 48, 101.

The Clemmensen reduction of water-insoluble substrates may be facilitated by adding a cosolvent such as ethanol, acetic acid, or dioxane.[‌15‌,‌31‌,‌32‌] However, increasing the solubility of the organic material in the reaction medium leads, in many cases, to increased side-product formation. Reduction of a 4-fluorenyl-4-oxobutanoic acid derivative to give butanoic acid ‌5‌ using amalgamated zinc in a mixture of concentrated hydrochloric acid and ethanol is illustrated in ‌Scheme 8‌.[‌15‌]

‌Meeeee 8‌ Meeeeeeee ee e Meeeee eeee Meee ee Meeeeeeeeeee Meeeeeeeeeee Meee/Meeeeee[‌88‌]

Meeeeeeee eeee eeee ee eeeeeeeeeeee eeeeeeeeeeee eeee/eeeeeee eee eeee eeeeeee ee eee eeeeeeeeeeeee ee eeeeeee eeeeeee eeeeeeee. Meeeeee eeeeeee eee eeeeeeee eeee ee eee eeeee ee eeeeeeeee M8, M8, M88, M88, M88, eee M88 eee eeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee eeeeeeeeeee ee eeee eee.[‌88‌–‌88‌] Mee eee eeeee ee (88M)-eeeeeee-8-ee-8β-ee (eeeeeeeee; ‌Meeeee 8‌), eeeeee ee eee eeee ee ee eeeeeeee eeeeee, ee eeeeeee eeee eeee eeee ee eeeeeeeeeeee eeeeeeeeeeee eeee/eeeeeee ee eeee eee eeeeeeeeee eeeeeeeeee ‌8‌.[‌88‌,‌88‌] Mee eeeeee eee eeee eeee eeee eee eee eeeeeeeeeee ee eeeeeeeee- ee eeeeeee-eeeeeee eeeeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeee ee (88M)-Meeeeee-8-ee-8β-ee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-(8M-Meeeeee-8-ee)eeeeeeee Meee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8-(8M-eeeeeee-8-ee)-8-eeeeeeeeeee eeee (88 e, 8.88 eee), eeeeeeeeeee Me (888 e), MeMM (888 eM), eee eeeee MMe (888 eM) eee eeeeee eeeee eeeeee eee 8 e. M eeeeee eeeeeee ee eeeee MMe (888 eM) eee eeeee eee eeeeeeeee eee eeeeeeeee eee 8 e. Meeee eeeeeee, eee eeeee eee eeeeeeeee eee eeeeee ee 8% ee MeMM (8 M) eeeee eee eeeeeee eeeeeeee eee eeeeeeeee. Mee eeee eee eeeeeeee eee eeeeeeeee, eeeeeee ee eee eeeeeee ‌8‌; eeeee: 88 e (888%); ee 888–888°M.

(88M)-Meeeeee-8-eee-8β,88β,88-eeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

Meeee MMe (88 eM) eee eeeee eeeeeeee eeee 88 eee ee e eeeeeee ee (88M)-eeeeeee-8-ee-8β-ee (8.88 e, 8.88 eeee), Me eeee (8.8 e, 88.8 eeee), eee eee MeMM (88 eM) eeee eee eeeeeee eee eeeeee eeeee eeeeee. Meeee 88 eee, eee eeeeeee eee eeeeee eee eee eeeee eee eeeeeee ee eeeeeeeeee. M8M eee eeeee ee eee eeeeeeee eeeee e eeeeeeeeeee eeeeeeee. Mee eeee eee eeee eeeeee eeeee eeeeeeeeeee eee eeee ee eeeeeeeeeee. Mee eeeeeeee eeee eeeeeeeee eee eeeee; eeeee: 8.88 e (88%).

References

Meeeeee Meeeeeeeeee

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