164731-35-5

Basic information

• Product Name: Benzeneethanol, a-(1,1-dimethylethyl)-2-(hydroxymethyl)-
• CAS NO: 164731-35-5
• Molecular Formula: C13H20O2
• Molecular Weight: 208.301
• Mol File: 164731-35-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzeneethanol, a-(1,1-dimethylethyl)-2-(hydroxymethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanol, a-(1,1-dimethylethyl)-2-(hydroxymethyl)-(164731-35-5)
• EPA Substance Registry System: Benzeneethanol, a-(1,1-dimethylethyl)-2-(hydroxymethyl)-(164731-35-5)

Safety Data

• Hazardous Substances Data: 164731-35-5(Hazardous Substances Data)

Upstream product

• 630-19-3 pivalaldehyde 
• 66-25-1 hexanal 
• 496-14-0 1,3-dihydroisobenzofuran 

Relevant articles and documents

Reductive electrophilic substitution of phthalans and ring expansion to isochroman derivatives

Reductive cleavage of phthalan, 1a, with Li metal in the presence of a catalytic amount of naphthalene leads to the formation of a stable aromatic dilithium compound. The adducts of the latter with CO2, aldehydes or ketones undergo ring closure to isochroman derivatives, leading to ring expansion of the original heterocycle. The reductive electrophilic substitution procedure was successfully extended to the substituted phthalans 1b and 1c, to afford the corresponding isochroman-3-ones in satisfactory yields.

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.

Electron-transfer-induced reductive cleavage of phthalans: Reactivity and synthetic applications

The behavior of phthalan (1a) was investigated under conditions of electron transfer from alkali metals in aprotic solvents. Reaction with lithium in the presence of a catalytic amount of naphthalene in THF led to the reductive cleavage of an arylmethyl carbon-oxygen bond, with formation of a stable dilithium compound. Trapping of this intermediate with several electrophiles (alkyl halides, carbonyl derivatives, CO2) was successful. The extension of this procedure to several substituted phthalans (1b-i) was investigated, and the regiochemistry as well as the synthetic usefulness of these reactions are discussed.