5452-03-9

Basic information

• Product Name: 4-tert-butylcyclohexyl benzoate
• CAS NO: 5452-03-9
• Molecular Formula: C₁₇H₂₄O₂
• Molecular Weight: 260.3713
• Mol File: 5452-03-9.mol

Chemical Properties

• Boiling Point: 341.2°C at 760 mmHg
• Flash Point: 155°C
• Density: 1.01g/cm³
• Vapor Pressure: 8.15E-05mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 4-tert-butylcyclohexyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-tert-butylcyclohexyl benzoate(5452-03-9)
• EPA Substance Registry System: 4-tert-butylcyclohexyl benzoate(5452-03-9)

Safety Data

• Hazardous Substances Data: 5452-03-9(Hazardous Substances Data)

Upstream product

• 582-25-2 Potassium benzoate 
• 21862-63-5 trans-4-tert-butylcyclohexanol 
• 937-05-3 cis-4-tert-butyl-1-cyclohexanol 
• 18508-90-2 trans-4-tert-butylmesyloxycyclohexane 
• 17265-04-2 cesium benzoate 
• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 614-16-4 Benzoylacetonitrile 
• 93-97-0 benzoic acid anhydride 
• 79345-29-2 sodium alkoxide of trans-4-tert-butylcyclohexanol 
• 100-39-0 benzyl bromide 
• 79345-28-1 sodium alkoxide of cis-4-tert-butylcyclohexanol 

Relevant articles and documents

Catalytic conversion of ketones to esters: Via C(O)-C bond cleavage under transition-metal free conditions

The catalytic conversion of ketones to esters via C(O)-C bond cleavage under transition-metal free conditions is reported. This catalytic process proceeds under solvent-free conditions and offers an easy operational procedure, broad substrate scope with excellent selectivity, and reaction scalability. This journal is

Iron(III) tosylate catalyzed acylation of alcohols, phenols, and aldehydes

Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.

Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride

The use of imidate esters as potential replacements for diethyl azodicarboxylate and triphenylphosphine in the Mitsunobu reaction is described. A series of secondary alcohols were allowed to react with (chloromethylene)dimethylammonium chloride, generated from dimethylformamide (DMF) and oxalyl chloride, to give imidate esters. Reaction of these salts with potassium benzoate or potassium phthalimide gave the products of SN2 substitution in excellent yields with clean inversion of stereochemistry. Optimization of reaction conditions is discussed as a means to increase the atom economy of the process by minimizing the quantity of nucleophile required.

Hypervalent (tert-butylperoxy)iodanes generate iodine-centered radicals at room temperature in solution: Oxidation and deprotection of benzyl and allyl ethers, and evidence for generation of α-oxy carbon radicals

1-(tert-Butylperoxy)-1,2-benziodoxol-3(1H)-one (1a) oxidizes benzyl and allyl ethers to the esters at room temperature in benzene or cyclohexane in the presence of alkali metal carbonates. Since this reaction is compatible with other protecting groups such as MOM, THP, and TBDMS ethers, and acetoxy groups, and because esters are readily hydrolyzed under basic conditions, this new method provides a convenient and effective alternative to the usual reductive deprotection. Oxidation with 1a occurs readily with C-H bonds activated by both enthalpic effects (benzylic, allylic, and propargylic C-H bonds) and/or polar effects (α-oxy C-H bonds), generating α-oxy carbon-centered radicals, which can be detected by nitroxyl radical trapping. Measurement of the relative rates of oxidation for a series of ring-substituted benzyl n-butyl ethers 2d and 2p-s indicated that electron-releasing groups such as p-MeO and p-Me groups increase the rate of oxidation, and Hammett correlation of the relative rate factors with the σ+ constants of substituents afforded the reaction constant ρ+ = -0.30. The large value of the isotope effect obtained for the oxidation of benzyl n-butyl ether 2d (k(H)/k(D) = 12-14) indicates that the rate-determining step of the reactions probably involves a high degree of benzylic C-H bond breaking. The effects of molecular dioxygen were examined, and the mechanism involving the intermediacy of the tert-butylperoxy acetal 5 and/or the hydroperoxy acetal 32 is proposed. Particularly noteworthy is the finding that (tert-butylperoxy)iodane 1a can generate the tert-butylperoxy radical and the iodine-centered radical 33a, even at room temperature in solution, via homolytic bond cleavage of the hypervalent iodine(III)-peroxy bond.

Nucleophilic Substitution of (Alkoxymethylene)dimethylammonium Chloride with Carboxylate Salts: a Convenient Procedure for the Synthesis of Esters with Inversion of Configuration

Secondary alcohols are converted into benzoate esters with inversion of configuration via sequential reaction with (chloromethylene)dimethylammonium chloride and potassium benzoate.