71029-37-3

Upstream product

• 99-89-8 4-Isopropylphenol 
• 106-95-6 allyl bromide 

Downstream Products

• 74663-59-5 2-allyl-4-isopropylphenol 
• 74663-51-7 2,6-di-n-Propyl-4-isopropylphenol 
• 74663-60-8 2,6-Diallyl-4-isopropylphenol 
• 74663-58-4 allyl 2-allyl-4-isopropylphenyl ether 
• 1448537-49-2 (S)-3-(4-isopropylphenoxy)-propane-1,2-diol 
• 1450760-88-9 (S)-2-(5-isopropyl-2,3-dihydrobenzofuran-2-yl)-1-phenylethanone 

Relevant academic research and scientific papers

Functionalized Allyl Aryl Ether Synthesis from Benzoic Acids Using a Dearomatization and Decarboxylative Allylation Approach

A strategy toward the preparation of substituted allyl aryl ethers from benzoic acids via a dearomatization and decarboxylative allylation (DcA) reaction is presented. The benzoic acids undergo a dearomatization to give alkylated 2,5-cyclohexadienyl ketoesters which are subjected to a palladium-catalyzed DcA reaction, providing a variety of functionalized allyl aryl ethers. In addition, the combination of a resonance stabilized DcA reaction with a Claisen rearrangement for the synthesis of multisubstituted phenols and applying to dihydroplicatin B derivative synthesis is also presented.

Chiral para-alkyl phenyl ethers of glycerol: Synthesis and testing of chirality driven crystallization, liquid crystal, and gelating properties

A series of enantiopure and racemic p-alkylphenyl glycerol ethers 1a-k were synthesized. A new, sensitive, and pictorial method of comparison of the IR spectra of solid enantiopure and racemic samples was developed to obtain preliminary information on the crystallization types of these compounds. In order to detect the subtle differences in the organization of the chiral solid phase, a new easily implemented approach, based on a chromatographic measuring of the relative abundance of the enantiomers in a single solution in equilibrium with a solid sample of arbitrary (0 ee 1) composition, is reported. One new conglomerate compound (Alk = n-Pr) and one borderline case (Alk = n-Bu) are disclosed. Higher members of the series of 1 (starting with an n-Bu derivative) are turned into liquid crystals upon melting; no significant differences between racemic and non-racemic samples were found. Only enantiopure methyl-, n-butyl, n-pentyl, n-hexyl, and n-heptyl substituted 1 were able to form supramolecular gels in hydrocarbon solvents; all racemic ethers 1 did not show such ability.

Enantioselective synthesis of benzofurans and benzoxazines via an olefin cross-metathesis-intramolecular oxo-Michael reaction

Chiral phosphoric acid and Hoveyda-Grubbs II were found to catalyze an olefin cross-metathesis-intramolecular oxo-Michael cascade reaction of the ortho-allylphenols and enones to provide a variety of benzofuran and benzoxazine derivatives in moderate to good yields and enantioselectivity.

Thermodynamic, spectroscopic, and density functional theory studies of allyl aryl and prop-1-enyl aryl ethers. Part 1. Thermodynamic data of isomerization

A chemical equilibration study of the relative thermodynamic stabilities of seventy isomeric allyl aryl ethers (a) and (Z)-prop-1-enyl aryl ethers (b) in DMSO solution has been carried out. From the variation of the equilibrium constant with temperature the Gibbs energies, enthalpies, and entropies of isomerization at 298.15 K have been evaluated. Because of their low enthalpies, the (Z)-prop-1-enyl aryl ethers are strongly favored at equilibrium, the Gibbs energies of the a→b isomerization ranging from -12 to -23 kJ mol-1. The entropy contribution is negligible in most reactions, but occasionally small positive values less than +10 J K-1 mol-1 of the entropy of isomerization are found. The equilibration studies were also extended to involve two pairs of related isomeric ethers with a Me substituent on C(2) of the olefinic bond. The Me substituent was found to increase the relative thermodynamic stability of the allylic ethers by ca. 3.4 kJ mol-1.

Alumina-Catalyzed Reactions of Hydroxyarenes and Hydroaromatic Ketones. 9. Reaction of Phenol with 1-Propanol

At 250-350 deg C in the presence of alumina, phenol (1) reacts with excess 1-propanol to give mainly (>90percent) C-alkylation to form mono- to penta-n-propylphenols plus some O-alkylations to form n-propyl aryl ethers. The principal component of the product mixture from 1 is 2,6-di-n-propylphenol (26-50 mol percent yield). With 4-n-propylphenol as substrate (instead of 1), tri-, tetra-, and penta-n-propylphenols are formed in 48-79percent combined yield. On the average, only 3percent of the total C3H7 groups in the product mixture are isopropyl ones. Deoxygenation is not observed. It is proposed that the principal products result from an SN2-type reaction mechanism which involves nucleophilic attack (variously by C-2, C-4, C-6, or O) of an adsorbed ambident phenoxide ion onto C-1 of an adsorbed n-propoxide group. n-Propylation at C-3 and C-5 of the phenol ring results from surface-catalyzed dienone-phenol rearrangement.Isopropylation may occur via a side reaction of SN1 type.