62836-20-8

Usage

Type of compound

Chlorinated derivative of 4-methyl-4-penten-2-ol

Usage

Synthetic intermediate in organic chemistry

Physical state

Colorless liquid

Odor

Chloroform-like

Primary use

Manufacture of other chemical compounds

Flammability

Flammable

Health hazards

Causes irritation to skin, eyes, and respiratory tract

Safety guidelines

Must be stored and handled according to proper safety guidelines

Upstream product

• 25308-82-1 1,1,1-trichloro-4-methyl-4-penten-2-ol 
• 130307-82-3 4-Brom-2-dichlormethyl-4-methyl-tetrahydrofuran 
• 130307-73-2 4-Brom-2-trichlormethyl-4-methyl-tetrahydrofuran 

Downstream Products

• 134835-46-4 4-Methyl-2-p-tolyloxy-pent-4-enal 
• 130307-82-3 4-Brom-2-dichlormethyl-4-methyl-tetrahydrofuran 
• 130307-79-8 trans-2-Dichlormethyl-4-ethoxy-4-methyl-tetrahydrofuran 
• 130307-79-8 cis-2-Dichlormethyl-4-ethoxy-4-methyl-tetrahydrofuran 
• 135644-65-4 4-Methyl-2-m-tolyloxy-pent-4-enal 
• 134835-45-3 4-Methyl-2-phenoxy-pent-4-enal 

Relevant academic research and scientific papers

Electrochemistry of 2-Trichloromethyl-tetrahydrofurans

4-Alkoxy-2-trichloromethyl-4-methyl-tetrahydrofurans (2) were prepared by anodic oxidation of 1,1,1-trichloro-4-methyl-pent-4-en-2-ol (1) in presence of bromide ions and bases.Electroreductions of these compounds in LiCl/methanol lead to 2-dichloromethyl-tetrahydrofurans (6).Under acidic conditions an olefin (10) was formed as main product.

Electrochemical Reduction of Trichloroacetaldehyde-Olefin-Addition-Products

Trichloroacetaldehyde reacts with different olefins forming addition products.In most cases this reaction results in 1,1,1-trichloro-2-hydroxy compounds (2a-d).But also a different route of reaction is possible.Thus 2,3-dimethylbut-1-ene (1e) forms 4-trichloro-1,1,2-tetrahydroxyfurane (2e) and cyclohexene (1f) forms 3-trichloromethyl-2-oxabicyclo-2,2,2-octane (2f).All addition products are suitable starting materials for electrochemical conversions.In acidic electrolytes, on lead cathodes the electrochemical reduction results in a simultaneous cleavage of a C-Cl and a C-O bond to form the CH=CCl2-group (3a-f).In neutral electrolytes, on mercury cathodes, however, a reductive conversion of a CCl3-group to a CHCl2-group takes place (4c, 4f).