95418-58-9

Usage

Uses

4-tert-Butoxystyrene is used in organic synthesis. It is used to synthesize 4'-tert-butoxy-biphenyl-4-carboxylic acid methyl ester.

Synthesis

Preparation of 4-tert-Butoxystyrene (3-tert-Butoxystyrene). To a 2000-mL three-necked round-bottom flask equipped with a dropping funnel, thermometer, reflux condenser, paddle stirrer and nitrogen inlet were placed 19.4 g (0.80 mol) of magnesium turnings and enough freshly dried and distilled tetrahydrofuran (THF) to cover the turnings. There were then added dropwise with stirring a solution of 143.3g (0.78 mol) of freshly distilled 4-bromostyrene (bp 46-47°C (0.03 mm)) in 500mL of THF. After 20mL of the 4-bromostyrene had been added, an exothermic reaction set in and was maintained between 25 and 35°C by adjusting the rate of addition of the bromo compound and with the aid of an ice bath. After the addition had been completed, the reaction mixture was heated to 60°C for 0.5h. Using a NaC1-ice bath, the mixture was cooled to 0°C and a solution of 100.88g (0.52 mol) of tert-butyl peroxybenzoate in 200 mL of THF was added via the dropping funnel at such a rate that the reaction temperature was maintained between 0 and 5°C. After completion of the addition, the reaction mixture was stirred at 25°C for 2 h. The organic layer was separated from the solid magnesium benzoate by decantation and the volume of the solution reduced on a rotary evaporator. The yellow oil that remained was washed with 1000 mL of 3% aqueous HCl solution and the organic layer separated. The aqueous layer was washed with two 200-mL portions of ether, and the ether and organic layers were combined and together washed with two 75-mL portions of a 10% NaOH solution followed by washing with water until the aqueous washings were neutral. After the solution was dried over Na2S04 and the ether was removed via a rotary evaporator, the remaining pale yellow oil was purified by fractional distillation in the presence of a few milligrams of ionol (2,6-ditert-butyl-4-methylphenol) as an inhibitor. There were obtained 46 g (50% yield, bp 45°C (0.02 mm)) of 4-tert-Butoxystyrene having the following elemental analysis.

References

Living cationic sequential block copolymerization of isobutylene with 4-tert-butoxystyrene: synthesis and characterization of poly(p-hydroxystyrene-b-isobutylene-b-p-hydroxystyrene) triblock copolymers. Bouchékif, H.; Som, A.; Sipos, L.; Faust, R.; Journal of Macromolecular Science, Part A: Pure and Applied Chemistry (2007), 44(4), 359-366.

InChI:InChI=1/C12H16O/c1-5-10-6-8-11(9-7-10)13-12(2,3)4/h5-9H,1H2,2-4H3

Upstream product

• 1104636-73-8 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione 
• 18995-35-2 4-tert-butoxychlorobenzene 
• 4363-34-2 vinylboronic acid 
• 67-71-0 dimethylsulfone 
• 51503-08-3 (4-(tert-butoxy)phenyl)methanol 
• 79-10-7 acrylic acid 
• 329318-60-7 1-(tert-butoxy)-4-iodobenzene 

Relevant academic research and scientific papers

Iron-Catalyzed Direct Julia-Type Olefination of Alcohols

Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- A nd N-heterocyclic compounds) that can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation/double dehydrogenation. Mechanistic study shows that the cleavage of the C-H bond of alcohol is the rate-determining step.

Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2

A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported.

Light driven decarboxylative cross coupling of acrylic acid and iodobenzene using [Mo132] type keplerate as a catalyst

Photochemical decarboxylative cross coupling reaction is one of the most significant research areas in industrial chemistry. Many research groups working on the topic use a photoredox catalyst merged with another coordination catalyst. The major problem in this case is the cost of such a cooperative catalyst system. Thus, to reduce the cost of the catalyst, designing a self-sufficient catalyst system is required. In our present work we have synthesized a giant molybdenum based polyoxometalate which acts as a photocatalyst as well as a coordination catalyst. We have shown that acrylic acid gets decarboxylated in the presence of UV light and gets coupled with iodobenzene to form styrene with maximum yield of 62%. The catalyst material is also stable under the reaction conditions and hence it is reusable.

SLOW RELEASE OF ORGANOBORONIC ACIDS IN CROSS-COUPLING REACTIONS

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1-B-T; where R1 represents an organic group, T represents a conformationalIy rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a pal ladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.