57792-36-6

Upstream product

• 552840-61-6 4-n-hexyloxy-2-methylphenyl chloride 
• 59-50-7 4-Chloro-3-methylphenol 
• 111-25-1 1-bromo-hexane 
• 1193-18-6 3-methylcyclohexen-2-one 
• 111-27-3 hexan-1-ol 
• 591-24-2 3-Methylcyclohexanone 
• 108-39-4 3-methyl-phenol 

Downstream Products

• 1162128-55-3 3-chloro-1-(2-(hexyloxy)-4-methylphenyl)propan-1-one 
• 1162128-13-3 3-chloro-1-(4-(hexyloxy)-2-methylphenyl)propan-1-one 

Relevant academic research and scientific papers

Conversion of Cyclohexanones to Alkyl Aryl Ethers by Using a Pd/C–Ethylene System

The conversion of cyclohexanone and substituted cyclohexanones into alkyl aryl ethers by using a Pd/C–ethylene system is discussed, with ethylene functioning as a hydrogen acceptor. The ether products are easily transformed into the corresponding phenols by treatment with BBr3. The direct conversion of cyclohexenone into phenol in the presence of a catalytic amount of Pd/C under an ethylene atmosphere is also described.

The Use of Ureates as Activators for Samarium Diiodide

A novel mode of SmI2 activation has been developed using ureates as reaction promoters. Several ureates formed by treatment of the corresponding ureas with n-BuLi have been shown to activate SmI2 to a substantial extent toward the reduction of 1-chlorodecane. Complexes formed from SmI2 and various ureates have been shown to be useful for the reduction of a variety of organohalides, including substrates of low reactivity such as aryl fluorides. Because of ease of synthesis and low molecular weight, the conjugate base of triethylurea (TEU-) was of primary focus. Visible spectroscopy and reactivity data are consistent with the hypothesis that the same complex is being formed when SmI2 is combined with either 2 or 4 equiv of TEU-, in spite of the greater reactivity of SmI2/4 TEU- with some alkyl halides. We propose that the active reductant is an N,O chelate formed between SmI2 and 2 equiv of TEU-.

Heterogeneous palladium-catalyzed synthesis of aromatic ethers by solvent-free dehydrogenative aromatization: Mechanism, scope, and limitations under aerobic and non-aerobic conditions

Starting from cyclohexanone derivatives and alcohols, both non-aromatic precursors, aryl ethers could be synthesized in good yields and with good selectivities in the presence of a catalytic amount of Pd/C, in one step, without added solvent, in a reaction vessel open to air. For less reactive substrates, the addition of 1-octene in a closed system under non-aerobic conditions improved the conversion. In addition, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. The process was also used with tetralone derivatives and polyols. Several reactions were performed to propose a mechanism for this transformation. The formation of an enol ether followed by a dehydrogenation reaction seem to be the key steps of this reaction. Aryl ethers were prepared in good yields and with good selectivities in a solvent-free and heterogeneous catalytic dehydrogenative alkylation of cyclohexanones with various alcohols. Three different complementary routes were used, and for the first time, non-aerobic, safe conditions could be used. Moreover, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. Copyright

Straightforward heterogeneous palladium catalyzed synthesis of aryl ethers and aryl amines via a solvent free aerobic and non-aerobic dehydrogenative arylation

Aryl ethers have been prepared from cyclohexanone derivatives and various alcohols in the presence of a catalytic amount of palladium on charcoal. The formation of an enol ether followed by an aerobic or non-aerobic dehydrogenation reaction, seem to be the key steps of this transformation. In addition, this new method was also adapted for the synthesis of arylamines.

Improvement of pharmacological properties of irreversible thyroid receptor coactivator binding inhibitors

We have previously reported the discovery and preliminary structure activity relationships of a series of β-aminoketones that disrupt the binding of coactivators to TR. However, the most active compounds had moderate inhibitory potency and relatively high cytotoxicity, resulting in narrow therapeutic index. Additionally, preliminary evaluation of in vivo toxicology revealed a significant dose related cardiotoxicity. Here we describe the improvement of pharmacological properties of thyroid hormone receptor coactivator binding inhibitors. A comprehensive survey of the effects of substitutents in key areas of the molecule was carried out based on mechanistic insight from the earlier report. This study revealed that both electron withdrawing and hydrophobic substituents on the aromatic ring led to higher potency. On the other hand, moving from an alkyl to a sulfonyl alkyl side chain led to reduced cytotoxicity. Finally, utilization of amine moieties having low pKa's resulted in lowered ion channel activity without any loss of pharmacological activity.

New synthetic method of aromatic ethers under microwave irradiation in dry media

Under microwave irradiation a number of phenols react remarkably fast with a number of primary alkyl halides to give aromatic ethers.

Alkylarylketo acids

Disclosed are novel alkylarylketocarboxylic acids and 5-substituted tetrazoles represented by the formula STR1 wherein Z is aryl or an alkyl of the structure STR2 W is a carboxyl moiety or a tetrazole moiety bound to Z at the 5-position of the tetrazole; R1 is C4 -C12 alkyl where Z is aryl and X is oxygen or is C5 -C12 alkyl where Z is alkyl and where Z is aryl and X is a bond; R2 and R3 are each independently hydrogen, C1 -C4 alkyl, hydroxy, C1 -C4 alkoxy, halogen, trihalomethyl, nitro, cyano or C1 -C4 acyl; R4, R5, R6 and R7 are each independently hydrogen or C1 -C4 alkyl or R4 and R6 or R5 and R7 can combine to form a carbocyclic ring; X is oxygen, or a bond at the ortho or para position; m is 0, 1 or 2; and n is 0 or 1, and nontoxic, pharmaceutically acceptable addition salts and carboxylic acid esters thereof.