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

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

TRIMETHYLENEMETHANE DIANION EQUIVALENT IN AQUEOUS MEDIUM

Via an indium mediated Barbier-type reaction in aqueous medium, carbonyl compounds react with a trimethylenemethane dianion equivalent to give the corresponding diols.

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

Straightforward synthesis of perhydrofuro[2,3-b]furans through a wacker-type reaction

An efficient synthesis of substituted perhydrofuro[2,3-b]furans has been accomplished from readily accesible 3-methylidene-1,5-diols based on an intramolecular acetalisation under Wacker-type reaction conditions.

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.

Polyphenylene as an electron transfer catalyst in lithiation processes

The lithiation of different functionalised chlorinated materials (1a-c), dichlorinated compounds (1d-f) and benzofused cyclic ethers (1g,h) with lithium powder in the presence of catalytic amounts of either linear (LPP) or crosslinked (CPP) polyphenylene, in THF at temperatures ranging between -78 and 20°C, leads to the expected organolithium intermediates (Ia-h), which by reaction with electrophiles [ButCHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe, Me3SiCl] gives, after hydrolysis with water, the expected products 2aa-hf.

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.

Substituted 1,7-dioxabicyclo[3.3.0]octanes: New easy access to the perhydrofurofuran core of aflatoxins and analogues

The reaction of 3-chloro-2-(chloromethyl)-1-propene (1) with lithium and a catalytic amount of naphthalene in the presence of different carbonyl compounds in THF a -78°C affords, after hydrolysis, the corresponding methylenic diols 2, which by a tandem hydroboration-oxidation with hydrogen peroxide followed by treatment with PCC (for ketone derivatives) or RuCl2(PPh3)3 (for aldehyde derivatives) yields the expected perhydrofurofurans 3.

Naphthalene-catalysed lithiation of 3-chloro-2-chloromethylpropene in a Barbier-type process with carbonyl compounds

The reaction of 3-chloro-2-chloromethylpropene (1) and carbonyl compounds (2) with an excess of lithium powder in the presence of a catalytic amount of naphthalene (6%) in tetrahydrofuran at -78 to 20°C leads, after hydrolysis, to the corresponding methylenic 1,5-diols 3 in a Barbier-type process. The treatment of the crude diols 3 with 12 M. hydrochloric acid affords selectively the corresponding substituted dihydropyrans 6.