Related Experiment Video
Updated: Aug 16, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Progress in C-C and C-Heteroatom Bonds Construction Using Alcohols as Acyl Precursors
Feng Zhao1, Bin Tan1, Qing Li1
1Hunan Provincial Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, China.
Abstract:
Acyl moiety is a common structural unit in organic molecules, thus acylation methods have been widely explored to construct various functional compounds. While the traditional Friedel-Crafts acylation processes work to allow viable construction of arylketones under harsh acid conditions, recent progress on developing acylation methods focused on the new reactivity discovery by exploiting versatile and easily accessible acylating reagents. Of them, alcohols are cheap, have low toxicity, and are naturally abundant feedstocks; thus, they were recently used as ideal acyl precursors in molecule synthesis for ketones, esters, amides, etc. In this review, we display and discuss recent advances in employing alcohols as unusual acyl sources to form C-C and C-heteroatom bonds, with emphasis on the substrate scope, limitations, and mechanism.
Related Concept Videos
Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Aldehydes and Ketones with Alcohols: Hemiacetal Formation
C–C Bond Formation: Aldol Condensation Overview
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Acid-Catalyzed Dehydration of Alcohols to Alkenes

