142052-59-3

Basic information

• Product Name: Cyclohexanol, 1,1'-(2-methylene-1,3-propanediyl)bis-
• CAS NO: 142052-59-3
• Molecular Formula: C16H28O2
• Molecular Weight: 252.397
• Mol File: 142052-59-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Cyclohexanol, 1,1'-(2-methylene-1,3-propanediyl)bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol, 1,1'-(2-methylene-1,3-propanediyl)bis-(142052-59-3)
• EPA Substance Registry System: Cyclohexanol, 1,1'-(2-methylene-1,3-propanediyl)bis-(142052-59-3)

Safety Data

• Hazardous Substances Data: 142052-59-3(Hazardous Substances Data)

Upstream product

• 15378-31-1 3-bromo-2-(bromomethyl)-1-propene 
• 108-94-1 cyclohexanone 
• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 

Relevant articles and documents

Synthesis of substituted 1,6-dioxaspiro[3.4]octanes from 3-Chloro- 2(chloromethyl)prop-1-ene

The naphthalene-catalysed lithiation of 3-chloro-2-(chloromethyl)prop-1- ene, in the presence of symmetrically substituted ketones, led to the corresponding methylenic homoallylic diols, which upon treatment with iodine and silver(I) oxide in dioxane/wate

Naphthalene-catalysed lithiation of 3-chloro-2-chloromethyl-propene: A barbier-type practical alternative to the trimethylenemethane dianion

The reaction of equimolar amounts of 3-chloro-2-chloromethylpropene (2) and a carbonyl compound (3) with an excess of lithium powder and a catalytic amount (6%) of naphthalene in tetrahydrofuran at -78°C leads, after hydrolysis with water, to the correspo

Lithiation reactions catalyzed by linear and cross-linked arene-based polymers. Generation of functionalized organolithium compounds

Lithiation of various substrates, such as chlorinated acetals, α-chloro ether, dichloro derivatives benzo-fused heterocycles, and allyl and benzyl derivatives, with excess lithium powder in the presence of a catalytic amount of soluble linear or insoluble cross-linked arene (naphthalene or biphenyl)-based polymers yields the expected organolithium intermediates. The latter react with electrophiles either in two steps or under Barbier-type reaction conditions to afford the corresponding adducts. The catalyst is easily recuperated by filtration at the end of the process, and the procedure can be regarded as a reasonable alternative to the use of free arenes as electron carrier in lithiation reactions.

Polymer supported arene-catalysed lithiation reactions

The reaction of functionalised mono or dichlorinated materials 1a-6a with an excess of lithium and a catalytic amount of a naphthalene (P(N)) or biphenyl (P(B)) supported polymer (easily prepared by radical copolymerisation of 2-vinylnaphthalene or 4-vinylbiphenyl with vinylbenzene and divinylbenzene) in THF either in the presence or not of different electrophiles [Me3SiCl, (i)prCHO, PhCHO, Et2CO, (CH2)4CO, (CH2)5CO, (c- C3H5)2CO, (i)Pr2CO, PhCOMe, PhCH=NPh] at -78 or -50°C leads, after hydrolysis with water, to the expected functionalised products 1ca-6ck. The polymeric catalyst is quantitatively recovered and can reused several times without any loss of activity.