Science of Synthesis

Lin, S.; Yan, L.; Liu, P., Science of Synthesis, (2007) 20, 96.

The oxidation of aldehydes to carboxylic acids using freshly prepared silver(I) oxide is normally carried out under basic conditions,[‌11‌,‌12‌] the reagent being generated in situ from silver nitrate and aqueous sodium hydroxide.[‌13‌,‌14‌] Acetone and alcohols such as methanol and ethanol are frequently used as the cosolvents in these oxidations two examples of which are shown in ‌Scheme 3‌. In the first the acid ‌5‌ is formed in 70% yield from the corresponding aldehyde,[‌12‌] and in the second the steroidal acid ‌7‌ is obtained from the aldehyde ‌6‌ in 76% yield.[‌14‌]

‌Meeeee 8‌ Meeeeeeee ee Meeeeeeee ee Meeeeeeeee Meeee Meeee Meeeee(M) Meeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

8β-Meeeeeeeeeeeee-8-eee-88-eeeeeeeeee Meee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

88% ee MeMM (88 eM) eee eeeee ee MeMM8 (8.8 e, 88 eeee) ee eeeeeeeee M8M (88 eM), eeeeeee eee eeeeeeeee eeeeeeeeee ee e eeeee eeeeeeeeeee. Mee MM8MM (88 eM) eee eeeeee eeeee ee eeee eeeeeeeeee eeeeee e eeeee eeee ee eeeee e eeee ee eee eeeeeeee ‌8‌ (8 e, 8.8 eeee) ee MeMM (88 eM) eee eeeeeeeeee. Mee eeeeeee eee eeeeeee ee 88–88°M eee 8 e, eee eeee eeeeee eeee eee eeeee, eeeeeeeee eeee 88% ee MMe, eee eeeeeeeee eeee MeMMe. Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeee eeeee eeeee-eeee eeeeeeee. Mee eeeeeeee eeeeee eeeeee eee eeeeeeeeeeee (MeMM/M8M) ee eeeeeee; eeeee: 888 ee (88%); ee 888–888°M (eee); [α]Mee −88 (e 8.8, MeMM).

References

Meeeeee Meeeeeeeeee

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