100791-76-2

Basic information

• Product Name: (4R,5R)-2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester
• Synonyms: (4R,5R)-2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester
• CAS NO: 100791-76-2
• Molecular Weight: 324.331
• Mol File: 100791-76-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (4R,5R)-2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester(100791-76-2)
• EPA Substance Registry System: (4R,5R)-2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester(100791-76-2)

Safety Data

• Hazardous Substances Data: 100791-76-2(Hazardous Substances Data)

Upstream product

• 13171-64-7 Dimethyl D-tartrate 
• 121-97-1 4-Methoxypropiophenone 
• 608-68-4 dimethyl L-tartrate 
• 497-19-8 sodium carbonate 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 100791-83-1 Dimethyl (4R,5R)-2-[(S)-1-bromoethyl]-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate 
• 100791-84-2 Dimethyl (4R,5R)-2-[(R)-1-bromoethyl]-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate 
• 100791-83-1 (4S,5S)-2-((S)-1-Bromo-ethyl)-2-(4-methoxy-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 100791-83-1 (4S,5S)-2-((R)-1-Bromo-ethyl)-2-(4-methoxy-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Enantioselective synthesis of α-bromo acid derivatives and bromohydrins from tartrate derived bromoacetals

Bromination of the acetals 4 derived from aryl alkyl ketones, ArCOR, and (2R,3R)-tartaric acid results in bromoacetals 5 with 78-90% de. Hydrolysis of those compounds with Ar = 4-methoxyphenyl or 3-bromo-4-methoxyphenyl results, after recrystallisation, in α-bromoketones 8 with 66-98% ee which are shown to undergo the Baeyer-Villiger oxidation to α-bromoesters 9 with minimal racemisation, α-Bromoketone 8d is shown to undergo carbonyl reduction to threo-bromohydrin 15 with retention of stereochemistry.

Tartaric Acid, an Efficient Chiral Auxiliary: New Asymmetric Synthesis of 2-Alkyl-2-arylacetic Acids

A highly enantioselective synthesis of 2-alkyl-2-arylacetic acids, an important class of antiinflammatory agents, based on a new diastereoselective α-bromination of homochiral acetals 1 and on the stereospecific silver-promoted rearrangement of the corresponding homochiral α-bromo acetals 2 and 3, is reported.The new methodology represents a meaningful example of the use of tartaric acid as efficient and economic chiral auxiliary.The asymmetric bromination of 1 is of general character and occurs with very high diastereoselectivity, even at room temperature; a mechanism for the new reaction is proposed.The overall process has been successfully applied to the preparation of enantiomerically pure 2-alkyl-2-arylacetic acids, among them (2S)-(+)-2-(6-methoxy-2-naphthyl)propanoic acid (Naproxen)