33426-70-9

Usage

InChI:InChI=1/C12H18O/c1-3-4-5-10-13-12-8-6-11(2)7-9-12/h6-9H,3-5,10H2,1-2H3

Upstream product

• 76429-82-8 1-Bromo-5-(2-bromo-4-methylphenoxy)pentane 
• 71-41-0 pentan-1-ol 
• 106-43-4 para-chlorotoluene 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 29540-83-8 p-tolyl triflate 
• 108-88-3 toluene 
• 110-89-4 piperidine 
• 110-00-9 furan 
• 6627-55-0 2-bromo-p-cresol 
• 111-24-0 1,5-dibromo-pentane 

Relevant academic research and scientific papers

Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights

A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.

An efficient copper-catalyzed etherification of aryl halides

An efficient and mild copper-catalyzed ether formation from aryl halides and aliphatic alcohols has been developed. The key to the successful coupling is the use of lithium alkoxide, directly or in situ generated by lithium tert-butoxide, and the corresponding alcohol as solvent. Georg Thieme Verlag Stuttgart - New York.

Oxygen Heterocycles by the Parham Cyclialkylation

The addition of butyllithium at -100 deg C to ω-bromoalkyl ethers of o-bromophenol (and its congeners) led to preferential exchange of the aryl bromine at position 2.The resulting organolithium reagents, under suitable conditions, cyclized to afford 2,3-dihydrobenzofurans (6), 3,4-dihydro-2H-1-benzopyrans (13), or 2,3,4,5-tetrahydro-1-benzoxepins (16) in good yields, but less satisfactory results were obtained with the intermediate expected to produce 8-methyl-3,4,5,6-tetrahydro-2H-1-benzoxocin (19). ω-Bromoethyl and ω-bromopropyl ethers of suitable dibromophenols were treated successively with 2 equiv of butyllithium and an electrophile to yield derivatives of 6 and 13.