2085-87-2

Basic information

• Product Name: Benzenemethanol, a-(ethoxymethyl)-a-methyl-
• CAS NO: 2085-87-2
• Molecular Formula: C11H16O2
• Molecular Weight: 180.247
• Mol File: 2085-87-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-(ethoxymethyl)-a-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(ethoxymethyl)-a-methyl-(2085-87-2)
• EPA Substance Registry System: Benzenemethanol, a-(ethoxymethyl)-a-methyl-(2085-87-2)

Safety Data

• Hazardous Substances Data: 2085-87-2(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 98-83-9 isopropenylbenzene 
• 98-86-2 acetophenone 
• 3188-13-4 ethyl chloromethyl ether 
• 1067-44-3 ethoxymethyltributyltin 
• 15561-33-8 1-chloro-2-phenylpropan-2-ol 

Downstream Products

• 7534-41-0 ethyl-(2-phenyl-allyl)-ether 
• 34713-70-7 2-Phenylpropanal 
• 104681-83-6 1-Methoxy-3-phenyl-butan-2-ol 
• 104681-83-6 1-Methoxy-3-phenyl-butan-2-ol 

Relevant articles and documents

4,4′-Di-tert-butylbiphenyl-catalysed lithiation of chloromethyl ethyl ether: A barbier-type new and easy alternative to ethyl lithiomethyl ether

The reaction of an equimolar amount of chloromethyl ethyl ether (1) and different carbonyl compounds (2) with an excess of lithium powder (1:7 molar ratio) in the presence of a catalytic amount of 4,4′-di-tert-butylbiphenyl (5 mol %) in THF at 0°C leads, after hydrolysis, to the corresponding hydroxyethers 3.

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.