211318-51-3

Basic information

• Product Name: Benzenepropanoic acid, a-diazo-b-hydroxy-2-methyl-, ethyl ester
• CAS NO: 211318-51-3
• Molecular Formula: C12H14N2O3
• Molecular Weight: 234.255
• Mol File: 211318-51-3.mol

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, a-diazo-b-hydroxy-2-methyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, a-diazo-b-hydroxy-2-methyl-, ethyl ester(211318-51-3)
• EPA Substance Registry System: Benzenepropanoic acid, a-diazo-b-hydroxy-2-methyl-, ethyl ester(211318-51-3)

Safety Data

• Hazardous Substances Data: 211318-51-3(Hazardous Substances Data)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 811467-22-8 3-hydroxy-2-oxo-3-o-tolyl-propionic acid ethyl ester 
• 811467-31-9 (+/-)-anti-ethyl 2,3-dihydroxy-3-(o-methylphenyl)propanoate 
• 51725-82-7 ethyl (2-methylbenzoyl)acetate 

Relevant articles and documents

DBU-catalyzed condensation of acyldiazomethanes to aldehydes in water and a new approach to ethyl β-hydroxy α-arylacrylates

DBU-catalyzed condensation of ethyl diazoacetate (EDA) with aldehydes in pure water afforded corresponding β-hydroxy α-diazo carbonyl compounds. The β-hydroxy group of the products was further converted into β-siloxy group. The Rh(II)-catalyzed reaction of the β-aryl β-siloxy α-diazo carbonyl compounds gave 1,2-aryl shift products predominantly. The three-step transformation constitutes an efficient synthesis of ethyl β-hydroxy α-arylacrylates.

Zinc derivative of ethyl diazoacetate in the synthesis of α-diazo-β- hydroxy esters

Addition of diethylzinc to ethyl diazoacetate generates a zinc derivative which adds to aldehydes to give α-diazo-β hydroxy esters.

Highly efficient and chemoselective direct aldol reaction of acyldiazomethane with aldehydes promoted by MgI2 etherate

Direct aldol condensation of various aromatic, heteroaromatic, α,β-unsaturated aldehydes and aliphatic aldehydes with acyldiazomethane was realized using MgI2 etherate (MgI2·(Et2O)n) as a promoter in the presence of diisopropyl amine (DIPEA) in excellent yields in a short time under mild conditions with high chemoselectivity. Iodide counterion, and a non-coordinating less ploar reaction media (i.e., CH2Cl2) are among the critical factors for this unique reactivity.

An efficient and convenient aldol addition of acyldiazomethane with aldehydes promoted by MgI2 etherate

The aldol addition of acyldiazomethane with aromatic aldehydes, vinyl aldehyde and aliphatic aldehydes was carried out efficiently in the presence of MgI2 etherate and iPr2EtN (DIPEA) using untreated reagent-grade CH2Cl2 under atmospheric conditions in good to excellent yields. Iodide counterion and a non-coordinating reaction media (i.e. CH2Cl2) are among the critical factors for the unique reactivity of this reaction system.

An efficient aldol-type reaction of ethyl diazoacetate with aldehydes promoted by MgI2 etherate

The first example of the preparation of α-diazo-β-hydroxy esters by the aldol-type condensation of aldehydes with ethyl diazoacetate using Et3N as base in the presence of magnesium iodide etherate [MgI2.(Et2O)n] has been achieved in good to excellent yields at room temperature in CH2Cl2 in 15-30 min.