7098-80-8

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C10H16O4/c1-7(2)9(11)12-5-8-6-13-10(3,4)14-8/h8H,1,5-6H2,2-4H3

Synthetic route

methacrylic acid methyl ester (80-62-6) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8)

Conditions	Yield
With titanium(IV) isopropylate; 1,4-phenylenediamine In cyclohexane for 15h; Heating;	67%
With methanol; sodium methylate; 1,1'-bi-2-naphthol
With titanium(IV) isopropylate transesterification;
Industry scale;
With dibutyltin dilaurate; hydroquinone at 110℃; for 8h;

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) + Methacryloyl chloride (920-46-7) → 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 48h;	64%

10H-phenothiazine (92-84-2) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8)

Conditions	Yield
With sodium carbonate	64%

2,3-Epoxypropyl methacrylate (106-91-2) + acetone (67-64-1) → 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8)

Conditions	Yield
With phosphoric acid at 60℃; Product distribution; Further Variations:; Catalysts; Cyclization;
With iron(III) chloride In hexane at 40℃; for 0.666667h; Ring cleavage; cyclization;

2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → 2,3-dihydroxypropyl methacrylate (5919-74-4)

Conditions	Yield
With acetic acid; 4-methoxy-phenol at 80℃; for 0.166667h;	80%
Hydrolysis; Acid hydrolysis;
With hydrogenchloride; water at 20℃; for 48h; Industry scale; Air stream;
With methanol; TEMPOL; 4-methoxy-phenol at 65℃; for 20h; Reagent/catalyst; Temperature;	73.1 %Chromat.

2-bromo-2-methyl propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)ethyl ester + 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → polymer, Mn=34500, Mw/Mn=1.15; monomer(s): glycerol-1-(methacrylate)-2,3-acetonide; 2-bromo-2-methylpropionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)ethyl ester

Conditions	Yield
With N-propyl 2-pyridylmethanimine; copper(I) bromide In toluene at 40℃;

2-bromo-2-methyl propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)ethyl ester + 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → polymer, Mn=6600, Mw/Mn=1.28; monomer(s): glycerol-1-(methacrylate)-2,3-acetonide; 2-bromo-2-methylpropionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)ethyl ester

Conditions	Yield
With N-propyl 2-pyridylmethanimine; copper(I) bromide In toluene at 40℃;

2-methyl-acrylic acid 3-trimethylsilanyl-propyn-2-ynyl ester (214268-06-1) + hostasol methacrylate (767357-31-3) + 2-bromo-2-methyl-propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl ester (1069117-44-7) + 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → polymer, Mn = 11.5 kDa, PDi = 1.15

Conditions

Yield

Stage #1: hostasol methacrylate; 2-bromo-2-methyl-propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl ester; 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester With N-propyl 2-pyridylmethanimine; copper(I) bromide In methoxybenzene at 20℃; Stage #2: 2-methyl-acrylic acid 3-trimethylsilanyl-propyn-2-ynyl ester With N-propyl 2-pyridylmethanimine; copper(I) bromide In methoxybenzene at 20℃; Further stages.;

2-bromo-2-methyl-propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl ester (1069117-44-7) + 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → α-oxanorbornenyl poly(solketal) methacrylate

Conditions	Yield
With N-propyl 2-pyridylmethanimine; copper(I) bromide In methoxybenzene at 20℃;

2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → 2-methyl-acrylic acid 7,7,9,9-tetrachloro-1,4-dioxa-6,8,10-triaza-5λ5,7λ5,9λ5-triphospha-spiro[4.5]deca-5,7,9-trien-2-ylmethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: Acid hydrolysis 2: hexachlorocyclotriphosphazene View Scheme

Upstream product

• 80-62-6 methacrylic acid methyl ester 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 106-91-2 2,3-Epoxypropyl methacrylate 
• 67-64-1 acetone 
• 920-46-7 Methacryloyl chloride 
• 92-84-2 10H-phenothiazine 

Downstream Products

• 5919-74-4 2,3-dihydroxypropyl methacrylate 

Relevant academic research and scientific papers

Dimethyl dioxin pentane ethanol methyl acrylate monomer and application (by machine translation)

The invention discloses a with ultraviolet cured role of dimethyl dioxin pentane ethanol methyl acrylate monomer and its application, dimethyl dioxin pentane ethanol methyl acrylate monomer is of the structural formula: the dimethyl dioxin pentane ethanol methyl acrylate monomer is a good light curing agent, can make use of the ultraviolet-curable modified epoxy acrylic resin oligomer, so as to form a cured film. (by machine translation)

Process for the Production of Diols

The invention relates to a process for the production of diols with a special structure which are characterized by formula (I). These diols are substances which, besides two OH groups, contain a C═C double bond so that they are suitable as monomers for the production of polymers. The process comprises hydrolyzing a corresponding cyclic precursor in aqueous medium in the presence of an acid dissolved in that medium, the hydrolysis being accompanied by the elimination of a carbonyl compound, and subsequently neutralizing the acid present in the reaction mixture with a base, the base having a pKb value above 0.18 and preferably above 3.0 and being present in heterogeneous form.

Formation of giant amphiphiles by post-functionalization of hydrophilic protein-polymer conjugates

A novel, generic method for the synthesis of families of tri-block protein-polymer giant amphiphiles was designed and developed. We have synthesized a hydrophilic α-maleimido poly-1-alkyne with Mn = 9.5 kDa (1H-NMR) and narrow PDi (1.15 as measured by SEC) via ATRP (Atom Transfer Radical Polymerization). This polymer was succesfully coupled to BSA to afford a hydrophilic multifunctional bioconjugate which was isolated using protein purification techniques and fully characterized. Following the post-functionalization approach, we introduced hydrophobicity to the resulting hydrophilic biohybrid by a straightforward, high yield "click"- chemistry cycloaddition step. The resulting tri-block protein-polymer amphiphiles were isolated and showed interesting aggregation patterns (TEM, confocal microscopy). The Royal Society of Chemistry 2007.

Effect of various factors on the reaction of glycidyl methacrylate with some carbonyl compounds

The effect of catalyst and its concentration, reaction temperature, solvent, and molar ratio of the reactants on the reaction of glycidyl methacrylate with some carbonyl compounds was studied.

Isolation and purification of dioxolanylmethyl methacrylates

A process was developed for isolation and purification of dioxolanylmethyl methacrylates prepared from glycidyl methacrylate and carbonyl compounds, with (2-methyl-1,3-dioxolan-4-yl)methyl methacrylate prepared from glycidyl methacrylate and paraldehyde as example.

New organofunctional cyclophosphazene derivatives

The rational design, synthesis and polymerization of the methacrylphosphazenes N3P3Cl5O(CHR)x(CHR′) yOC(O)CMe=CH2 (x=y=1,2, R=R′=H; x=1, R=Me, y=1, R′=H; x=1, R=H, y=1, R′=Me) is reported. Another new type of alkenyloxy derivative is prepared from 5-nonbornene-2-methoxide and N3P3Cl5. The preparation of spirocyclic derivatives with methacrylate or protected hydroxyl groups is reported Various functionalized ferrocene derivatives of the cyclophosphazenes have been prepared with particular attention being paid to the synthesis and electrochemical characterization of the N3P3Cl6-n(NMeCH2C5H 4FeC5H5)n(n=1,2,3,4) series.

Anionic living polymers, their derivatives and composition comprising them

The methacrylic ester polymers produced according to this invention are uniquely distinguished from the radically prepared polymers of similar composition by the fact that both polymers produced: by anionic living polymerization and by deactivating the active terminals of anionic living polymers; contain acetal and/or ketal groups as the blocked hydroxyl groups and have narrow molecular weight distribution. Hydroxyl group-containing methacrylic acid ester polymers are produced by hydrolysis of the above-mentioned polymers. The anionic living polymers are produced in high yields by anionically polymerizing methacrylic acid esters containing an acetal or ketal group in the presence of initiators such as alkaline metal alkoxides. The polymers of the present invention can be used in various fields of applications such as coatings and adhesives. The polymers of the present invention yield curable high solids compositions.

Transition-Metal-Catalyzed Asymmetric Organic Synthesis via Polymer-Attached Optically Active Phosphine Ligands. 13. Asymmetric Hydrogenation with Polymer Catalysts Containing Primary and Chiral Secondary Pendant Alcohols

The copolymerizations of (4S,5S)-2-p-styryl-4,5-bis-1,3-dioxolane with a cross-linking monomer, ethylene 1,2-dimethacrylate (7), and methacrylates bearing both a primary alcohol function and a chiral secondary alcohol function, (2S)-, (2RS)-, or (2R)-2,3-dihydroxypropyl methacrylate , gave polymers (6a-c, respectively) onto which rhodium was exchanged via the chloro(1,5-cyclooctadiene)rhodium(I) dimer.The resulting insoluble polymers containing chiral rhodium centers and the ancillary alcohol sites catalyzed the hydrogenation of olefins in ethanol to yield chiral N-acylamino acids and hydratropic acid.The catalyst containing the R alcohol (6a) gave amino acids in an optical yield that was 6percent higher than that obtained from polymer (6b) bearing the racemic alcohol and 8percent higher than that obtained from catalyst with the S alcohol when the reactions were performed in THF.