25772-85-4

Upstream product

• 150-76-5 4-methoxy-phenol 
• 106-89-8 epichlorohydrin 
• 2211-94-1 2,3-epoxypropyl p-methoxyphenyl ether 

Downstream Products

• 2211-94-1 4-methoxybenzyloxy ester of (S)-glycidol 
• 2211-94-1 (2S)-2-{[4-(methoxy)phenoxy]methyl}oxirane 
• 142036-87-1 Acetic acid 1-chloromethyl-2-(4-methoxy-phenoxy)-ethyl ester 
• 142037-06-7 (R)-1-Chloro-3-(4-methoxy-phenoxy)-propan-2-ol 
• 140696-03-3 (S)-1-chloro-3-(4-methoxyphenoxy)-2-propanol 
• 141987-52-2 Acetic acid (S)-1-chloromethyl-2-(4-methoxy-phenoxy)-ethyl ester 
• 140647-18-3 Acetic acid (R)-1-chloromethyl-2-(4-methoxy-phenoxy)-ethyl ester 

Relevant academic research and scientific papers

A phosphonium ylide as a visible light organophotoredox catalyst

A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.

Visible-light-triggered Catalytic Halohydrin Synthesis from Epoxides and Trichloroacetonitrile by Copper and Iron Salts

Preparation of vicinal halohydrins, in which copper or iron chlorides catalyze the ring-opening reaction of epoxides with visible light effectively, is described. The use of trichloroacetonitrile as a halogen source enables catalytic HCl generation under the mild conditions. This method can also be applied to the aziridine ring-opening reaction.

Protective opening of epoxide using pivaloyl halides under catalyst-free conditions

An efficient and environmentally benign protocol for protective opening of epoxide (POE) with pivaloyl halides in solvent-free conditions and in aqueous media under catalyst-free conditions has been developed. The green reaction conditions, simple work-up procedures, high yields and broad scope of the reaction illustrate the good synthetic utility of this method. The key advantages of the reaction are regioselectivity and reconvertability of products into their prior epoxides in the presence of mild reaction conditions.

Conversion of epoxides to β-chlorohydrins with thionyl chloride and β-cyclodextrin in water

Several epoxides are efficiently converted to the corresponding β-chlorohydrins in impressive yields with thionyl chloride in the presence of β-cyclodextrin using water as solvent at room temperature. Copyright Taylor & Francis, Inc.

Ionic liquid as reagent. A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst- and solvent-free conditions

A variety of structurally diverse epoxides undergo facile cleavages by ionic liquid, [AcMIm]X without any catalyst and solvent to produce the corresponding vicinal halohydrins in high yields. The cleavages are considerably fast and highly regioselective.

Green protocol for the synthesis of vicinal-halohydrins from oxiranes using the [Bmim]PF6/LiX reagent system

Epoxides undergo rapid ring-opening with lithium halides in [bmim]PF 6 or [bmim]BF4 ionic liquids under mild and neutral conditions to afford the corresponding vic-halohydrins in high to quantitative yields. The epoxides show enhanced reactivity in ionic liquids thereby reducing reaction times and improving the yields significantly. The recovered ionic liquid can be reused in three to four subsequent runs with consistent activity.

Difluorocarbene induced of facile synthesis of chlorohydrins from glycidyl ethers

A novel and unusual approach based on a ClCF2COONa-DMF system has been developed for the synthesis of chlorohydrins via an unexpected mechanism. In a first ever report for the synthesis of chlorohydrins from glycidyl ethers, e.g., CH2=CH-CH2-O-Z, CH 3CH2-O-Z, C6H5-O-Z, C 6H4(o-CH3)-O-Z, CH2=C(CH 3)C(=O)-O-Z, etc., (where Z = glycidyl), difluorocarbene-induced facile regioselective ring opening of epoxides has generated the compound in high yield (70%-83%).

Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin

Highly regioselective ring opening of epoxides to halohydrins has been carried out in impressive yields with hydrogen and lithium halides in presence of β-cyclodextrin using water as solvent.

RESOLUTION OF RACEMIC O-(4-METHOXYPHENYL)GLYCIDOL

Racemic O-(4-methoxyphenyl)glycidol has been resolved in three steps by employing lipase mediated kinetic acylation of the halohydrin intermediates.

HALOGENATED ETHERS. XV. KINETICS OF THE CATALYTIC REACTION OF p-METHOXYPHENOL WITH 1-CHLORO-2,3-EPOXYPROPANE

The kinetics of the reaction of p-methoxyphenol with 1-chloro-2,3-epoxypropane was invesigated.The partial rate constants and the limiting stage of the reaction were determined by the method employed in enzymatic catalysis.