79828-22-1

Basic information

• Product Name: Cyclohexanemethanol, a-methyl-2-methylene-
• CAS NO: 79828-22-1
• Molecular Formula: C9H16O
• Molecular Weight: 140.225
• Mol File: 79828-22-1.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexanemethanol, a-methyl-2-methylene-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanemethanol, a-methyl-2-methylene-(79828-22-1)
• EPA Substance Registry System: Cyclohexanemethanol, a-methyl-2-methylene-(79828-22-1)

Safety Data

• Hazardous Substances Data: 79828-22-1(Hazardous Substances Data)

Upstream product

• 591-49-1 1-methylcyclohex-1-ene 
• 123-63-7 paracetaldehyde 
• 103496-31-7 1-(dipropylborylmethyl)cyclohexene 
• 75-07-0 acetaldehyde 
• 103216-74-6 Cyclohex-1-enylmethyl-diethyl-borane 

Downstream Products

• 2047-97-4 2-methyl-1-acetyl-1-cyclohexene 
• 65756-02-7 2-methylenecyclohexyl methyl ketone 

Relevant articles and documents

Synthesis with Organoboranes; 4. Transformation of Olefins into Homoallylic Alcohols, β,γ- and α,β-Unsaturated Ketones via Allylic Diethylboranes

Allylic diethylboranes are obtained from 1-methylcycloalkenes and 2-alkenes, respectively, via metalation with trimethylsilylmethylpotassium (generated in situ from bis(trimethylsilylmethyl)mercury and potassium sand) and subsequent reaction with chlorodiethylborane.The allylic boranes react diastereoselectively with aldehydes to give homoallylic alcohols.The alcohols are oxidized with pyridinium dichromate to β,γ-unsaturated ketones, which in turn are isomerized with aluminum oxide to conjugated ketones.The transformation provides access to 2-methylene-1-acylcycloalkanes, 3-acyl-1-alkenes and 3-acyl-2-alkenes not readily available by Friedel-Crafts acylation of olefins.

A NEW GENERAL APPROACH TO 2-SUBSTITUTED METHYLENECYCLANES USING 1-(DIALKYLBORYLMETHYL)CYCLOALKENES

A novel method for the synthesis of 2-substituted methylenecyclopentanes and methylenecyclohexanes based on the allylboration of carbonyl compounds and alkoxyacetylenes with 1-(dialkylborylmethyl)cyclopentene and -cyclohexene is described.

DIMETHYLALUMINUM CHLORIDE CATALYZED ENE REACTIONS OF ALDEHYDES.

Dimethylaluminum chloride, which is a mild Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic and aromatic aldehydes with alkenes containing a disubstituted vinylic carbon. Proton-initiated rearrangements do not occur, since the alcohol-Lewis acid complex formed in the ene reaction reacts rapidly to give methane and a nonacidic aluminum alkoxide. Formaldehyde and excess Me//2AlCl give good yields of ene adducts with all types of alkenes. With 1 equiv of Me//2AlCl, formaldehyde and mono- and 1,2-disubstituted alkenes give gamma -chloro alcohols resulting from cis addition of chlorine and hydroxymethyl groups to the double bond. This work is pertinent to the synthesis of alcohols.