2276-46-2

Basic information

• Product Name: 1,2-Cyclohexanediol,1,2-diacetate
• Synonyms: 1,2-Cyclohexanediol,diacetate (6CI,7CI,8CI,9CI); NSC 563
• CAS NO: 2276-46-2
• Molecular Formula: C10H16 O4
• Molecular Weight: 200.235
• Mol File: 2276-46-2.mol

Chemical Properties

• CAS DataBase Reference: 1,2-Cyclohexanediol,1,2-diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclohexanediol,1,2-diacetate(2276-46-2)
• EPA Substance Registry System: 1,2-Cyclohexanediol,1,2-diacetate(2276-46-2)

Safety Data

• Hazardous Substances Data: 2276-46-2(Hazardous Substances Data)

Usage

Derivation

Derived from cyclohexanediol and acetic acid

Physical State

Clear, colorless liquid

Odor

Slightly sweet

Common Uses

a. Solvent
b. Intermediate in the synthesis of other organic compounds

Applications

a. Production of fragrances
b. Production of flavors
c. Pharmaceutical industry
d. Manufacture of plastics
e. Manufacture of adhesives
f. Manufacture of coatings

Toxicity

Low toxicity

Safety

Generally regarded as safe for use in various industrial processes

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 64-19-7 acetic acid 
• 110-83-8 cyclohexene 
• 110-82-7 cyclohexane 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 546-67-8 lead(IV) tetraacetate 
• 28141-32-4 2-Iodo-cyclohexanol 
• 1072-21-5 hexanedial 

Downstream Products

• 1165952-91-9 cyclohexa-1,3-diene 

Relevant articles and documents

Bu3SnH-Mediated Pinacol Coupling of 1,5- and 1,6-Dicarbonyl Compounds: Synthetic and Mechanistic Studies

A new method is described for the intramolecular pinacol coupling of 1,5- and 1,6-dicarbonyl compounds, employing Bu3SnH as the stoichiometric reductant. The key steps in this pinacol cyclization are the addition of a tin ketyl to a carbonyl group and a subsequent intramolecular SH2 reaction. The isolation of 1,3-dioxa-2-stannolanes, along with other product and labeling studies, provides strong support for the proposed homolytic substitution step, which distinguishes the pinacol cyclization from other reductive cyclizations of tin ketyls, all of which proceed through abstraction of hydrogen from Bu3SnH in the final step. An interesting consequence of the SH2 pathway is very high cis selectivity in the cyclization of 1,5-dicarbonyl compounds. Mechanistic studies furnish evidence that the steps that precede homolytic substitution, including C-C bond formation, are reversible under the reaction conditions.

PREPARATION OF DIESTERS OF (METH)ACRYLIC ACID FROM EPOXIDES

The application relates to a process for preparing a (meth)acrylic acid diester by reacting a (meth)acrylic acid anhydride with an epoxide in the presence of a catalyst system comprising a first and/or second catalyst in combination with a co-catalyst. The first catalyst is a halide of Mg or a trifluoromethanesulfonate of a rare earth element; the second catalyst is a Cr(lll) salt; and the co- catalyst is a tertiary amine, a quaternary ammonium salt, a tertiary phosphine or a quaternary phosphonium salt.

Mild organic ammonium tribromide-mediated regioselective ring opening of epoxides with alcohols, water, acetic anhydride, and amines under solvent-free reaction conditions

Organic ammonium tribromide (OATB), N-methylpyrrolidine-2-one hydrotribromide (MPHT) was found to be an efficient catalyst for the regioselective ring opening of epoxides with various nucleophiles under solvent free conditions. This procedure occurs under neutral and mild reaction conditions with out adding any additive and afforded high yields of products.

Acyloxylactonisations mediated by lead tetracarboxylates

The reaction of lead(IV) tetracarboxylates with carboxylic acids containing unsaturated side chains has been found to give acyloxy lactone products in a diastereoselective process; the reaction can be extended to lead(IV) tetrazolates to give the analogous outcome. Mechanistic implications of these results are discussed.

Alumina-supported molybdenum (VI) oxide: An efficient and recyclable heterogeneous catalyst for regioselective ring opening of epoxides with thiols, acetic anhydride, and alcohols under solvent-free conditions

An efficient and simple protocol for regioselective ring opening of epoxides with thiols, acetic anhydride, and alcohols using 16wt% MoO3 supported on alumina as a recyclable catalyst is described. Copyright

Zeolite catalyzed ring opening of epoxides to acetylated diols with acetic anhydride

HY Zeolite is found to be a versatile catalyst for opening of epoxides to the corresponding acetylated 1,2-Diols with acetic anhydride in good yields.

Process for the production of 1,2-bis (acyloxylates)

A process for the preparation of 1,2-bis(acyloxyates) comprises acylation of epoxides with carboxylic anhydrides in the presence of a catalytic composition containing a tertiary amine and a carboxylic acid. Preferably, the carboxylic acid is a conjugate acid of the carboxylic anhydride. The carboxylic acid acts as a co-catalyst and its use in conjunction with the tertiary amine significantly increases the rate of reaction and results in higher selectivity. The catalytic composition may be prepared prior to acylation or in situ providing application versatility.

Oxygenation of Oleefinic Hydrocarbons Catalyzed by Iron(II) Acetonitrile Solvate

Oxygenation reactions of olefins having an endo- or exo-cyclic double bond, namely, cyclohexene, norbornene, camphene, longifolene, and ent-kaurene, with a simple model reagent, Fe(MeCN)62+-H2O2-Ac2O, for mono-oxygenase were investigated in connection with their biotransformations.Keywords oxygenation; olefin; endo-cyclic double bond; exo-cyclic double bond; iron(II) acetonitrile solvate; hydrogen peroxide; model enzyme; mono-oxygenase

OXYGENATION OF AROMATIC AND ALIPHATIC HYDROCARBONS BY A NEW REAGENT SYSTEM, Fe(CH3CN)6(2+)-H2O2-Ac2O: AN EFFECTIVE MODEL REAGENT FOR MONO-OXYGENASE

Reactions of aromatic and aliphatic hydrocarbons with a new system, Fe(CH3CN)6(2+) - H2O2 - Ac2O in CH3CN, gave oxygenation products with fairly high reaction efficiency ( Tables I and II )compared to known to reagent systems used as enzyme models for mono-oxygenases.Investigations of the mechanism of these reactions indicated the involvement of either complex C.FeIV(OH)(OAc)(2+), or complex D, FeIV(OAc)(2+), dependig on the organic substrate.Keywords-oxygenation; aromatic hydrocarbon; aliphatic hydrocarbon; hexakisacetonitrile iron(II) perchlorate; hydrogen peroxide; enzyme model; mono-oxygenase

Electron-transfer Processes: Metal Salt Catalysed Oxidation of Olefins by Peroxydisulphate

The reaction of simple olefins (oct-1-ene, oct-2-ene, cyclohexene, cycloheptene) with peroxydisulphate has been investigated under several conditions: (i) in aqueous medium and catalysis by AgI, FeII, and CuII; (ii) in acetic madium and catalysis by CuII, FeIII; (iii) in the presence of traps of nucleophilic alkyl radicals (protonated heteroaromatic bases and 1,4-benzoquinone either in water or in acetic acid).The catalyst and the radical trap govern the selectivity and allow a variety of new synthetic achievements.Evidence for a unified initial mechanism of electron transfer with formation of a radical cation from the olefin is reported to explain all the results.In water the radical cation gives a β-hydroxyalkyl radical, which, depending on the nature of the catalyst and the trap, can give the corresponding saturated alcohol by hydrogen abstraction, the products of CuII oxidation, or β-hydroxyalkylation of the heteroaromatic compound or 1,4-benzoquinone.In acetic acid the radical cation gives a β-acetoxyalkyl radical, which is oxidized to the corresponding allylic acetate by copper(II) acetate or trapped by the heteroaromatic base.