2223-71-4

Basic information

• Product Name: 8-tert-butyl-1,4-dioxaspiro[4.5]decane
• Synonyms: 8-tert-butyl-1,4-dioxaspiro[4.5]decane;4-tert-Butylcyclohexanone ethylene acetal;4-t-butylcyclohexanone ethylene acetal
• CAS NO: 2223-71-4
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.30188
• EINECS: 218-739-4
• Mol File: 2223-71-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 241.9°C at 760 mmHg
• Flash Point: 93°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 0.0544mmHg at 25°C
• Refractive Index: 1.472
• CAS DataBase Reference: 8-tert-butyl-1,4-dioxaspiro[4.5]decane(CAS DataBase Reference)
• NIST Chemistry Reference: 8-tert-butyl-1,4-dioxaspiro[4.5]decane(2223-71-4)
• EPA Substance Registry System: 8-tert-butyl-1,4-dioxaspiro[4.5]decane(2223-71-4)

Safety Data

• Hazardous Substances Data: 2223-71-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 7274, 1993 DOI: 10.1021/jo00077a060Tetrahedron Letters, 29, p. 2215, 1988 DOI: 10.1016/S0040-4039(00)86715-5

InChI:InChI=1/C12H22O2/c1-11(2,3)10-4-6-12(7-5-10)13-8-9-14-12/h10H,4-9H2,1-3H3

Upstream product

• 107-21-1 ethylene glycol 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 55233-96-0 4-(1,1-dimethylethyl)cyclohex-3-en-1-one ethylene ketal 
• 75-21-8 oxirane 

Downstream Products

• 944-19-4 4-tert-butyl-1,1-dimethoxy-cyclohexane 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 2228-98-0 4-tert-butylcylohexene 
• 65157-14-4 2-(1-Benzyl-4-tert-butyl-cyclohexyloxy)-ethanol 
• 13294-73-0 1-tert-butyl-4-methylenecyclohexane 

Relevant articles and documents

Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl-Ene Reaction

An efficient desymmetrizing carbonyl-ene reaction of 1-substituted 4-methylenecyclohexanes with glyoxal derivatives was thus executed by a chiral N,N′-dioxide/NiII catalyst, providing facile access to cyclohexene derivatives bearing two remote 1,6-related stereocenters. This distal stereocontrol methodology originates from the efficient interaction between the catalyst with enophiles, discrimination of the two chair conformations of olefinic components, and the intrinsic six-membered transition-state structure of ene process.

Acidic properties of sulfonic acid-functionalized FSM-16 mesoporous silica and its catalytic efficiency for acetalization of carbonyl compounds

Propyl-sulfonic acid-functionalized FSM-16 mesoporous silica (SO 3H-FSM) is prepared by a conventional post-modification method. For the acetalization of carbonyl compounds with ethylene glycol, SO 3H-FSM shows a higher rate and 1,3-dioxolane yield than conventional heterogeneous solid acids such as zeolites, montmorillonite K10 clay, silica-alumina, and the sulfonic resin. SO3H-FSM is stable during the reaction, with no leaching and deactivation of sulfonic acid groups, and is reusable without loss of its activity. The acidity and hydrophilicity of SO 3H-FSM are well characterized by the microcalorimetry of NH 3 adsorption, NH3-TPD, and H2O-TPD, and the result is compared with those for various aluminosilicate zeolites (HZSM5, HBEA, HY) and K10 clay. It is found that NH3-TPD is not suitable for characterizing the acidity of SO3H-FSM, because the decomposition of SO3H groups on SO3H-FSM begins above 200°C. An NH 3 adsorption microcalorimetric experiment at 150°C shows that, compared with HZSM5, SO3H-FSM has a smaller number of acid sites but has a similar number of strong acid sites with ammonia adsorption heat above 140 kJ mol-1. Comparison of the structural properties and catalytic results shows that a large pore diameter and low hydrophilicity are required to obtain high activity. Bronsted acid sites with a relatively strong acid strength are more suitable for this reaction, but the high acid concentration is not indispensable. The high activity of SO3H-FSM should be caused by the presence of the strong Bronsted acid sites in the mesopore with a relatively low hydrophilicity, where both reactants can smoothly access the acid sites.

An efficient procedure for the preparation of cyclic ketals and thioketals catalyzed by zirconium sulfophenyl phosphonate

A convenient method for the preparation of cyclic ketals and thioketals using zirconium sulfophenyl phosphonate as catalyst is described.