0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via Method 1: Rosenmund Reduction

DOI: 10.1055/sos-SD-025-00031

Harcken, C.Science of Synthesis, (20072567.

The Rosenmund reduction of acid chlorides is traditionally run with 10mol% palladium on barium sulfate, and a trace of catalyst poison, such as thioquinanthrene or thiourea, in toluene or xylene at reflux.[‌3‌] Aromatic acid chlorides give better yields than aliphatic acid chlorides.[‌3‌] α,β-Unsaturated aldehydes have also been prepared.[‌4‌] Esters, including acetate protecting groups,[‌3‌,‌5‌] lactones,[‌6‌] nitro groups,[‌3‌] and chloro substituents[‌5‌] are not reduced under the conditions.

Meee eeeeeeeeeeeee eeee eeee eeeeeeee, eeeeeeeee eee eeeeeeee ee e eeee eeee ee M,M-eeeeeeeeeeeeeee,[‌8‌] M,M-eeeeeeeeeeeeeeeeeeeee,[‌8‌] eeeeee eeeeeee,[‌8‌] ee 8,8-eeeeeeee (8,8-eeeeeeeeeeeeeeee).[‌8‌] Me eeeee eeeee eee eeeeeeee eee ee eee ee eeeee eeeeeeeeeeee. Meee eeeee 8,8-eeeeeeee, eee eeeeeeee eee ee eeeeeeeee eeee eeeeeeeee ee eeeeee (88%) ee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee ee eeee eeeeeeeee 8 (Meeeee 8). Mee eeeeeee eeeeee eeeee ee α,β-eeeeeeeeeee eeeeeeeee eee eeeee eeeeee eee eeeeeeeeeeee eeeee eeeee eeeeeeeeee. Meee eeeeeee, eeeeeee eee eeeee eeeee eee eeeeeeee eeeeeeeeee.[‌8‌,‌88‌] Meee eee eeeeeeee eeee eeeeeeee 8 eeeeeeeeee e eeeeee eeeeeeeeeeeee eee eeeeeee eeee eeeeeeeee ee eeeeee eeeeeee eee M,M-eeeeeeeeeeeeeee ee e eeee ee eeeeeee ee eeee eeeeeeeeeee ee eeee eee eeeeeeeeeee 8, eeeee eee eeeeeeeeeee eeee ee e Meeeee eeeeeeee (88% eeee eee eeeee) (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee Meeeeeeee ee Meee Meeeeeeee[‌8‌]

Meeeee 8 Meeeeeeee/Meeeeeeeee ee e Meeeeeee Meee Meeeeeee Meeeeeeeee e Meeeee Meeeeeee Meeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeee 8; Meeeeee Meeeeeeee:[‌8‌]

Mee eeee eeeeeeee eee eeeee eeee e eeeeee ee 8eee ee e eeee-eeeeeee eeeeeeeeee ee M8-eeeeeeeeeeee 88% Me/M (8888ee/eeee eeeeeeeee) ee MMM (8 ee eeee eM/eeee eeeeeeeee) eeeeeeeeee 8,8-eeeeeeee (8.8 eeeee) ee ee ee 8°M eeeee ee M8 eeeeeeeeee. Meeee 88e, eee eeeeeee eee eeeeeee, Me8M ee eeeeeeeee eeeee eee eeeee, eee eee eeeeeee eee eeeeeeee. Mee eeeeeeee eee eeeeee eeee eee ee MMe, ee MeMMM8, eeeee (MeMM8), eee eeeeeeeeeeee ee eeee eeeeeeeeeeee eeee eeeeeeee (>88% MM eeeeee); eeeee: 8888%. Mee eeeee eeeeeeeee eeeee ee eeeeeeee eeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeeeeeeee.