Related Experiment Video
Updated: Jan 23, 2026

Synthesis of Plant Phenol-derived Polymeric Dyes for Direct or Mordant-based Hair Dyeing
Published on: December 1, 2016
One-Step Regioselective Synthesis of Benzofurans from Phenols and α-Haloketones
Bingqiao Wang1, Qiu Zhang2, Juan Luo3
1College of Pharmacy, Center for Lab Teaching and Management, Chongqing Medical University, No.1 Yixueyuan Road, Chongqing 400016, China. wwangkkang111@163.com.
Abstract:
Reported here is the direct synthesis of naphthofurans and benzofurans from readily available phenols and α-haloketones promoted by titanium tetrachloride which combines Friedel-Crafts-like alkylation and intramolecular cyclodehydration into one step. This simple protocol allows for the formation of a variety of high value naphthofurans and benzofurans within which a series of cyclic and acyclic groups are readily incorporated. This process demonstrates the advantages of high levels of regioselectivity, broad substrate scope, and moderate to excellent yields.
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Regioselectivity of Electrophilic Additions-Peroxide Effect
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Regioselective Formation of Enolates
Structure and Nomenclature of Alcohols and Phenols
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and...

