Related Experiment Video
Updated: Jul 12, 2026
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
The synthesis of(14)C- and (3)H-labeled glycerol ethers
E O Oswald1, C Piantadosi, C E Anderson
1Departments of Biochemistry and Medicinal Chemistry, University of North Carolina, Chapel Hill, North Carolina.
Abstract:
The racemic(14)C-and(3)H-labeled alpha and beta derivatives of octadecyl glycerol ether (batyl alcohol) and of hexadecyl glycerol ether (chimyl alcohol) of high specific activity were synthesized by treating the appropriate alkyl halides with a large excess of the potassium salts of isopropylidene or benzylidene glycerol. By use of the trifluoroacetic anhydride esterification procedure, the labeled diesters of alpha and beta octadecyl and hexadecyl glycerol ethers were prepared. The labeled monoesters of beta octadecyl and of beta hexadecyl glycerol ethers were isolated from the reaction mixtures by silicic acid column chromatography.
Related Concept Videos
02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
02:28Structure and Nomenclature of Ethers
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
02:35Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
02:15Preparation 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...
01:07Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
02:23Autoxidation of Ethers to Peroxides and Hydroperoxides