51835-45-1

Basic information

• Product Name: α-Methoxybenzenemethanol acetate
• Synonyms: Acetic acid α-methoxybenzyl ester
• CAS NO: 51835-45-1
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20048
• Mol File: 51835-45-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: α-Methoxybenzenemethanol acetate(CAS DataBase Reference)
• NIST Chemistry Reference: α-Methoxybenzenemethanol acetate(51835-45-1)
• EPA Substance Registry System: α-Methoxybenzenemethanol acetate(51835-45-1)

Safety Data

• Hazardous Substances Data: 51835-45-1(Hazardous Substances Data)

Upstream product

• 538-86-3 benzyl methyl ether 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 64-19-7 acetic acid 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-24-7 acetic anhydride 
• 35364-99-9 α-chlorobenzyl methyl ether 
• 127-09-3 sodium acetate 

Downstream Products

• 52117-33-6 4-methoxy-4-phenylbutan-2-one 
• 538-86-3 benzyl methyl ether 
• 14629-58-4 trimethyl(phenethyloxy)silane 
• 62559-35-7 5-Phenyl-2,2,8,8-tetramethyl-3,7-dioxa-2,8-disilanonane 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 60669-59-2 ethyl 3-methoxy-3-phenylpropanoate 

Relevant articles and documents

Co2(CO)8-catalyzed reactions of acetals or lactones with hydrosilanes and carbon monoxide. A new access to the preparation of 1,2-diol derivatives through siloxymethylation

The Co2(CO)8-catalyzed reaction of acetals with hydrosilanes and CO under mild reaction conditions (an ambient temperature under an ambient CO pressure), leading to the production of vicinal diols is reported. A siloxymethyl group can be introduced via the cleavage of one of two alkoxy groups in the acetal. The effects of the types of hydrosilanes, acetals, solvents, and reaction temperatures on the yield of siloxymethylation products were examined in detail. The reactivity for hydrosilanes is as follows; HSiMe3 > HSiEtMe2 > HSiEt2Me > HSiEt3. Hemiacetal esters are more reactive than dimethyl acetals. The polarity of the solvent used also has a significant effect on both the course of the reaction as well as the reaction rate. The site-selective siloxymethylation can be achieved in the case of cyclic acetals such as tetrahydrofuran (THF) and tetrahydropyrane (THP) derivatives, depending on the nature of the oxygen substituent attached adjacent to the oxygen atom in the ring. When 2-alkoxy THF or THP derivatives are used as substrates, the siloxymethylation takes place with cleavage of the ring C-O bond. In contrast, the reaction of 2-acetoxy THF or THP derivatives results in siloxymethylation with the cleavage of C-OAc bond. The ring-opening siloxymethylation of lactones was also examined.

Acid catalyzed rearrangement of vinyl and ketene acetals

Substituted vinyl and ketene acetals undergo smooth oxygen-to-carbon rearrangement with a catalytic amount of TMSOTf to afford chain-extended ketones or esters, respectively. The developed procedure has been applied to the stereoselective synthesis of C-glycosides from the corresponding anomeric vinyl ethers.