541-47-9

Basic information

• Product Name: 3,3-Dimethylacrylic acid
• Synonyms: (CH3)2C=CHCOOH;2-Butenoicacid,3-methyl-;3,3-Dimethylacrylsαure;3-methyl-2-butenoicaci;3-Methyl-2-butensαure;3-methyl-buten-2-oic-acid;3-methyl-crotonicaci;3-Methylcrotonsαure
• CAS NO: 541-47-9
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 208-782-7
• Product Categories: Organic acids;acid;Building Blocks;C1 to C5;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;fine chemicals
• Mol File: 541-47-9.mol
• Article Data: 57

Chemical Properties

• Melting Point: 65-70 °C(lit.)
• Boiling Point: 194-195 °C(lit.)
• Flash Point: 93°C
• Appearance: White prism-shape crystals
• Density: 0,969 g/cm3
• Vapor Pressure: 0.19mmHg at 25°C
• Refractive Index: 1.4226 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: pK1:5.12 (25°C)
• Water Solubility: Soluble in water, and methanol.
• BRN: 1720305
• CAS DataBase Reference: 3,3-Dimethylacrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Dimethylacrylic acid(541-47-9)
• EPA Substance Registry System: 3,3-Dimethylacrylic acid(541-47-9)

Safety Data

• Hazard Codes: Xi,C
• Statements: 37/38-41-34
• Safety Statements: 26-36/37/39-45-27
• RIDADR: 3261
• WGK Germany: 1
• RTECS: GQ5425000
• F: 21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 541-47-9(Hazardous Substances Data)

Usage

Description

May be prepared by the action of alkalis or bases on the ester of α-bromoisovaleric acid; by condensation of acetone with malonic acid or bromoacetic ester; by oxidation of mesityl oxide with sodium hypochlorite.

Chemical Properties

Different sources of media describe the Chemical Properties of 541-47-9 differently. You can refer to the following data:
1. 3-Methylcrotonic acid has green, phenolic, dairy aroma
2. White to brown crystal

Occurrence

Reported found in the rhizomes of Senecio kaempferi Seib.; the corresponding ester occurs naturally in waste wort. Also reported found in raspberries, wheat bread, cocoa, coffee, black tea, Arctic bramble, and green and roasted maté.

Uses

Chemical Intermediates.

Definition

ChEBI: A methyl-branched fatty acid that is but-2-enoic acid bearing a methyl substituent at position 3.

Preparation

By the action of alkalis or bases on the ester of α-bromoisovaleric acid; by condensation of acetone with malonic acid or bromoacetic ester; by oxidation of mesityl oxide with sodium hypochlorite.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3214, 1949 DOI: 10.1021/ja01177a079Organic Syntheses, Coll. Vol. 3, p. 302, 1955Tetrahedron Letters, 36, p. 2469, 1995 DOI: 10.1016/0040-4039(95)00285-K

Purification Methods

Crystallise the acid from hot water or pet ether (b 60-80o). [Beilstein 2 IV 1555.]

InChI:InChI=1/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)/p-1

Synthetic route

3-Benzenesulfinyl-3-methyl-butyric acid → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
In various solvent(s) for 0.0166667h; Irradiation;	99%

3,3-dimethyl acrylaldehyde (107-86-8) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;	98%
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube;	91%
With Iron(III) nitrate nonahydrate; oxygen; sodium 2,2,2-trifluoroacetate In ethyl acetate at 25℃; under 760.051 Torr; for 16h;	38%

(Z)-3-iodobut-2-enoic acid (34450-60-7) + methylmagnesium bromide (75-16-1) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
Stage #1: methylmagnesium bromide With zinc dibromide In diethyl ether at 25℃; Stage #2: (Z)-3-iodobut-2-enoic acid; dichloro bis(acetonitrile) palladium(II) In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide at 25℃; for 12h;	95%

carbon monoxide (201230-82-2) + 3-hydroxy-2-methyl-1-propene (513-42-8) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In 1,2-dimethoxyethane at 190℃; under 30400 Torr; for 48h;	92%

3-methyl-2-buten-1-ol (556-82-1) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With potassium phosphate; carbon dioxide; CrH6Mo6O24(3-)*3H3N*3H(1+) In dimethyl sulfoxide at 80℃; under 750.075 Torr; for 24h; Green chemistry;	89%
Multi-step reaction with 2 steps 1: 1-hydroxy-1,2-benziodoxole-3(1H)-one-1-oxide / dimethylsulfoxide / 16 h / 20 °C 2: NaOH; H2O / dimethylsulfoxide View Scheme

3-methyl-2-buten-1-ol (556-82-1) → 3-Methylbutenoic acid (541-47-9) + 3,3-dimethyl acrylaldehyde (107-86-8)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium acetate; 4,7-di-(NaSO3Ph)-[1.10]phenanthroline-Pd(OAc)2 In water at 100℃; under 22502.3 Torr; for 10h; pH=6.5 - 11.5;	A n/a B 88%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; titanium(IV) oxide In benzotrifluoride under 750.075 Torr; for 8h; Irradiation;
With oxygen In water at 20℃; under 760.051 Torr; for 336h; pH=6.5 - 7;

concentrated sodium bisulfite + 4-methyl-pent-3-en-2-one (141-79-7) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With sodium hypochlorite In chloroform; water	80%

3-Hydroxy-3-methylbutyric acid (625-08-1) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With toluene-4-sulfonic acid at 100 - 110℃; for 1h;	76%
With sulfuric acid
With sulfuric acid durch Destillation;

2-methyl-1-propenylbromide (3017-69-4) + carbon dioxide (124-38-9) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at -10℃; electrolysis with 3 F/mol at 10 mA/cm2; Pt cathode; Mg anode;	64%
With tetrabutylammonium tetrafluoroborate; (2,2'-bipyridine)nickel(II) dibromide In N,N-dimethyl-formamide at -10℃; Product distribution; electrolysis with 3 F/mol at 10 mA/cm2; Pt cathode, Mg anode; without/with catalyst;	64%

dimethyl 6-hydroxy-11-(1-methylethylidene)-9,10-dioxa-4,5-diazatricyclo[6.2.1.02,7]undec-3-ene-3,6-dicarboxylate → 3-Methylbutenoic acid (541-47-9) + pyridazine-3,6-dicarboxylic acid dimethyl ester (2166-24-7)

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In chloroform at -40 - 20℃;	A 57% B n/a

4-methyl-pent-3-en-2-one (141-79-7) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With sodium hypochlorite; lithium hypochlorite In ethanol at 77℃; for 8h;	56%
With sodium hydroxide; sodium bromite; sodium bromide In water at 0 - 45℃; for 2h;	40%
With potassium hydroxide; iodine

2-methyl-1-propenylbromide (3017-69-4) + carbon monoxide (201230-82-2) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With [bmim]PF6; triethylamine; bis-triphenylphosphine-palladium(II) chloride In water at 100℃; under 15001.2 Torr; for 20h;	56%
With sodium hydroxide; cetyltrimethylammonim bromide; nickel cyanide In toluene at 95℃; under 735.5 Torr; for 8h;	45%

4,4-dimethyloxetan-2-one (1823-52-5) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With sulfuric acid

ethyl 2-bromoisovalerate (609-12-1) → α-ethoxy-isovaleric acid ethyl ester (109989-35-7) + 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With ethanol; sodium ethanolate Bildung des Aethylesters;

ethyl 2-bromoisovalerate (609-12-1) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With N,N-diethylaniline Bildung des Aethylesters;
With quinoline at 170 - 175℃; und dann Erhitzen auf185-190grad;Bildung des Aethylesters;
With quinoline at 225℃; Bildung des Aethylesters;
With potassium hydroxide

cycl-isopropylidene malonate (2033-24-1) + acetic anhydride (108-24-7) → 3-Methylbutenoic acid (541-47-9)

4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester (101080-10-8) → 3-Methylbutenoic acid (541-47-9) + 4-Methylpyrazol-3-carbonsaeure-methylester (68809-58-5)

Conditions	Yield
at 140 - 190℃;

ethyl isodehydroacetate (3385-34-0) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With potassium hydroxide

iodoform (75-47-8) + sodium isobutoxide (13259-29-5) → 3-Methylbutenoic acid (541-47-9)

iodoform (75-47-8) + sodium isobutoxide (13259-29-5) → formic acid (64-18-6) + 3-Methylbutenoic acid (541-47-9) + α-isobutoxy-isobutyric acid (17860-06-9) + isobutyric Acid (79-31-2)

Conditions	Yield
Produkt 5-8:Methylisobutylaether;Methylendiisobutylaether;Isobutylen;1,2-Diisobutoxy-2-methyl-propan-1-ol;

phorone (504-20-1) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
bei unvollstaendiger Ozonisation entstandenes Produkt reagiert mit Wasser;
With chloroform; ozone und Umsetzen das Reaktionsprodukt mit Wasser;

ethyl 3-hydroxy-3-methylbutanoate (18267-36-2) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
durch Wasserabspaltung und Verseifung des Reaktionsprodukts;
With formic acid
With potassium pyrosulfate at 140 - 145℃; Bildung des Aethylesters;
Verseifen des Esters nach Wasserabspaltung;
With phosphorus trichloride Bildung des Aethylesters;

ethyl 2-acetyl-3-methylbut-2-enoate (35044-52-1) → 3-Methylbutenoic acid (541-47-9) + acetic acid (64-19-7)

Conditions	Yield
With barium dihydroxide

2-bromoisovaleric acid (10323-40-7, 565-74-2) + sodium methylate (124-41-4) → 2-methoxy-3-methylbutanoic acid (66018-25-5) + 3-Methylbutenoic acid (541-47-9)

2-bromoisovaleric acid (10323-40-7, 565-74-2) → 2-methoxy-3-methylbutanoic acid (66018-25-5) + 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With sodium methylate

2-bromoisovaleric acid (10323-40-7, 565-74-2) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
With quinoline zunaechst auf 140-150grad und dann auf 165-170grad;
With ammonium hydroxide nachfolgendes Zerlegen mit Baryt und Ansaeuern mit Schwefelsaeure;

1,1,1-trichloro-3,3-dimethyl-3-bromopropane (23153-21-1) + sodium ethanolate (141-52-6) → 3-Methylbutenoic acid (541-47-9)

3-methylbut-2-enal (100191-34-2) → 3-Methylbutenoic acid (541-47-9) + 4-methyl-2-oxo-pent-3-enoic acid (143255-96-3)

Conditions	Yield
With potassium hydroxide; ethanol; silver nitrate

4-chloro-2-methylbut-3-yn-2-ol (29552-15-6) → 3-Methylbutenoic acid (541-47-9)

Conditions	Yield
ueber 4-Chlor-2-methyl-but-1-en-3-in;

3-Methylbutenoic acid (541-47-9) + tert-butylisonitrile (119072-55-8, 7188-38-7) + isovaleraldehyde (590-86-3) → 1-(tert-butylamino)-4-methyl-1-oxopentan-2-yl 3-methylbut-2-enoate

Conditions	Yield
In water for 0.5h; Passerini reaction; Sonication; Cooling with ice;	100%
In water at 25℃; Kinetics; Further Variations:; Solvents; Reagents; Passerini reaction;	95%
In water at 20℃; Passerini reaction;	86%
In dichloromethane at 25℃; for 18h; Kinetics; Product distribution; Further Variations:; Solvents; Passerini reaction;	45%

3-Methylbutenoic acid (541-47-9) + p-chlorobenzylisocyanide (39546-47-9) + isovaleraldehyde (590-86-3) → C18H25ClN2O2 (1262749-10-9)

Conditions	Yield
With ammonia In methanol; water at 130℃; for 1.5h; Ugi reaction; Microwave irradiation; microwave tube;	100%

3-Methylbutenoic acid (541-47-9) → 3,3-Dimethylacryloyl chloride (3350-78-5)

Conditions	Yield
With oxalyl dichloride In dichloromethane at 20℃;	99%
With thionyl chloride at 0℃; for 3h;	96%
With thionyl chloride 1.) reflux, 1.3 h, 2.) room temperature, 2.5 h, 3.) reflux, 1 h;	92%

3-Methylbutenoic acid (541-47-9) + phenylmethanethiol (100-53-8) → 3-methyl-3-(phenylmethylthio)butanoic acid (7536-39-2)

Conditions	Yield
With hydrogenchloride In piperidine	99%
With piperidine for 24h; Heating;	90%
With piperidine for 22h; Heating;	81%

3-Methylbutenoic acid (541-47-9) + benzyl bromide (100-39-0) → benzyl 3-methylbut-2-enoate (37526-89-9)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In chloroform for 18h; Heating;	99%
With caesium carbonate In N,N-dimethyl-formamide	87%
With potassium hydroxide; tetrabutylammomium bromide In chloroform; water for 18h; Reflux; Inert atmosphere;	417 mg

3-Methylbutenoic acid (541-47-9) + benzyl alcohol (100-51-6) → benzyl 3-methylbut-2-enoate (37526-89-9)

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In benzene for 38h; Heating;	99%
With iron(III)-acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene for 14h; Inert atmosphere; Reflux;	95%
With TiO(acac)2 In xylene for 36h; Heating;	93%
With di-tert-butyl-diazodicarboxylate; polymer-bound triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 12h; Mitsunobu reaction;	87%
With di-tert-butyl-diazodicarboxylate; triphenylphosphine polystyrene beads In tetrahydrofuran at 20℃; for 12h; Mitsunobu reaction;	87%

3-Methylbutenoic acid (541-47-9) + (1R,2R,3S,6R,8R,9R)-3-methoxy-1,8,12,12-tetramethyl-4-oxatricyclo[6.4.0.0(2,6)]dodecan-9-ol (102358-40-7) → (1R,2R,3S,6R,8R,9R)-3-methoxy-1,8,12,12-tetramethyl-4-oxatricyclo[6.4.0.0(2,6)]dodecan-9-yl 3-methylbut-2-enoate (102358-39-4)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 24h;	99%
Stage #1: 3-Methylbutenoic acid; (1R,2R,3S,6R,8R,9R)-3-methoxy-1,8,12,12-tetramethyl-4-oxatricyclo[6.4.0.0(2,6)]dodecan-9-ol With dmap; dicyclohexyl-carbodiimide In toluene at 0 - 20℃; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 9h;	6.5 mg

3-Methylbutenoic acid (541-47-9) + 3,5-Dimethylphenol (108-68-9) → 4,4,5,7-tetramethyl-3,4-dihydrocoumarin (40662-14-4)

Conditions	Yield
With methanesulfonic acid In toluene at 85℃; for 4h; Inert atmosphere;	99%

3-Methylbutenoic acid (541-47-9) + Trimethylhydroquinone (700-13-0) → 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin (40662-76-8)

Conditions	Yield
With methanethiosulfonic acid at 70℃; for 1.5h;	98%
With methanesulfonic acid at 70℃; for 4h;	87%
With methanesulfonic acid at 85℃; for 3h;	85%

3-Methylbutenoic acid (541-47-9) → 3-methyl-2-butenoic anhydride (34876-10-3)

Conditions	Yield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 0.5h;	98%
With potassium carbonate; 2-(4-nitrobenzenesulfonyl)-4,5-dichloropyridazin-3-one In tetrahydrofuran at 40℃; for 3h;	92%
With triethylamine; trichloroacetonitrile; triphenylphosphine In dichloromethane at 20℃; for 4h;	75%

3-Methylbutenoic acid (541-47-9) + recorcinol (108-46-3) → 7-hydroxy-2,2-dimethyl-chroman-4-one (17771-33-4)

Conditions	Yield
With phosphorus pentoxide In methanesulfonic acid at 70℃; for 0.333333h; Friedel-Crafts Acylation; Inert atmosphere; Microwave irradiation;	98%
With methanesulfonic acid; phosphorus pentoxide at 70℃;	96%
With methanesulfonic acid; phosphorus pentoxide at 70℃; for 0.5h;	94%

3-Methylbutenoic acid (541-47-9) + benzene (71-43-2) → 3-methyl-3-phenylbutanoic acid (1010-48-6)

Conditions	Yield
With aluminum (III) chloride at 5 - 20℃; for 0.333333h;	98%
With aluminium trichloride at 65℃;	94%
Stage #1: 3-Methylbutenoic acid; benzene; aluminum (III) chloride at 65℃; Stage #2: With hydrogenchloride; water at 0℃; pH=< 2;	94%

Thiophene-2-thiol (7774-74-5) + 3-Methylbutenoic acid (541-47-9) → 3-methyl-3-(thiophene-2-thio)butyric acid (111190-17-1)

Conditions	Yield
With triethylamine In tetrahydrofuran for 21h; Heating;	98%
With triethylamine In tetrahydrofuran for 20h; Reflux; Inert atmosphere;	63.35%
With triethylamine In tetrahydrofuran for 20h; Reflux; Inert atmosphere;	63.35%
With triethylamine In tetrahydrofuran for 20h; Inert atmosphere; Reflux;	63.35%
With triethylamine In tetrahydrofuran for 20h; Inert atmosphere; Reflux;	63.4%

N-p-toluenesulfonylpyrrole (17639-64-4) + 3-Methylbutenoic acid (541-47-9) → 4,5-dihydro-4,4-dimethyl-1-(4'-methylphenylsulfonyl)cyclopenta[b]pyrrol-6(1H)-one

Conditions	Yield
With {[Zn4(pdpa)2(H2O)8]*H2O}n; trifluoroacetic anhydride In 1,2-dichloro-ethane for 4h; Reagent/catalyst; Nazarov Cyclization; Reflux;	98%
With C10H2N16(4-)*3H2O*4Ag(1+); trifluoroacetic anhydride In 1,2-dichloro-ethane for 5h; Reagent/catalyst; Nazarov Cyclization; Reflux;	92%
With iron(III) chloride; trifluoroacetic anhydride In dichloromethane for 4h; Reflux;	74%
With trifluoroacetic anhydride In 1,2-dichloro-ethane at 80℃; for 16h; Nazarov cyclization;	51%

{TiMgCl6(C2H5O2CCH3)4} + 3-Methylbutenoic acid (541-47-9) → Ti(4+)*Mg(2+)*4Cl(1-)*2(CH3)2CCHCO2(1-)*2C2H5O2CCH3={TiMgCl4((CH3)2CCHCO2)2(C2H5O2CCH3)2}

Conditions	Yield
In dichloromethane dissolving (TiMgCl6(C2H5O2CCH3)4) (3.2 mmol) in CH2Cl2; addn. of (CH3)2CCHCO2H (6.5 mmol) against a stream of N2; warming to 35°C for 1.5 h; cooling to room temp.;; pumping off solvent; stirring with hexane; filtering, drying in vac. for 2 h; elem. anal.;;	98%

3-Methylbutenoic acid (541-47-9) + (3-isopropylene-2,2-dimethylcyclobutyl)methanol → (2,2-dimethyl-3-(propan-2-ylidene)cyclobutyl)methyl 3-methylbut-2-enoate

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 40℃; for 24h;	98%

methanol (67-56-1) + 3-Methylbutenoic acid (541-47-9) → Methyl 3,3-dimethylacrylate (924-50-5)

Conditions	Yield
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate for 3h; Reflux; Green chemistry;	97.8%
With sulfuric acid	95%
With sulfuric acid for 16h; Heating;	92%

3-Methylbutenoic acid (541-47-9) + <(4-nitrophenyl)oxy>sulfonyl isocyanate (73748-48-8) → (4-nitrophenyl)-N-(3-methylbut-2-enoyl)sulfamate (1070898-27-9)

Conditions	Yield
With triethylamine In toluene at 20℃; for 0.5h;	97%

3-Methylbutenoic acid (541-47-9) + recorcinol (108-46-3) → 1-(2',4'-dihydroxyphenyl)-3-methyl-1-oxo-2-butene (99323-00-9)

Conditions	Yield
With zinc(II) chloride; trichlorophosphate at 25℃; for 2h;	96.9%
With aluminium trichloride; trichlorophosphate for 5h; Ambient temperature;	92%
Stage #1: 3-Methylbutenoic acid With boron trifluoride diethyl etherate; trichlorophosphate at 0℃; for 0.25h; Substitution; Stage #2: recorcinol at 25℃; for 5h; Acylation; Friedel-Crafts reaction;	80%

3-Methylbutenoic acid (541-47-9) + thiophenol (108-98-5) → 3-methyl-3-phenylsulfanyl-butanoic acid (64793-86-8)

Conditions	Yield
With tetrabutyl ammonium fluoride at 50℃; for 24h;	96%
With iodine at 50℃; for 5h; Michael reaction;	95%
With piperidine at 103 - 107℃; for 19h;	87%

3-Methylbutenoic acid (541-47-9) + dimethyl sulfoxide (67-68-5) → 3-Methyl-but-2-enoic acid methylsulfanylmethyl ester (72064-63-2)

Conditions	Yield
With t-butyl bromide; sodium hydrogencarbonate at 25 - 30℃; for 24h;	95%
With t-butyl bromide; sodium hydrogencarbonate

3-Methylbutenoic acid (541-47-9) + 3-Phenyl-1-propanol (122-97-4) → 3-phenylpropyl 3-methyl-2-butenoate (56500-48-2)

Conditions	Yield
With chloro-trimethyl-silane; silver perchlorate; titanium tetrachloride; 4-(trifluoromethyl)benzoic anhydride In dichloromethane; toluene at 20℃; for 12h;	95%
With 2-fluoro-1-ethylpyridinium tetrafluoroborate; cesium fluoride 1) methylene chloride, 30 min, r.t., 2) methylene chloride, overnight, r.t.; Yield given. Multistep reaction;

3-Methylbutenoic acid (541-47-9) + methoxyhydroquinone (824-46-4) → 2,2-Dimethyl-6-hydroxy-7-methoxy-4-chromanone (74094-44-3)

Conditions	Yield
With methanesulfonic acid at 70℃; for 12h;	95%
With methanesulfonic acid; phosphorus pentoxide at 70℃; for 0.5h;	91%
With methanesulfonic acid; phosphorus pentoxide	91%
With trifluoroacetic acid at 80℃; for 1h;	84%
With PPA 1.) 30 deg C, 4 h, 100 deg C, 1 h;	48%

3-Methylbutenoic acid (541-47-9) + 3-Ethoxy-4-methoxybenzenethiol (111424-64-7) → 3-(3-Ethoxy-4-methoxy-phenylsulfanyl)-3-methyl-butyric acid (111424-50-1)

Conditions	Yield
With piperidine at 103 - 107℃; for 18h;	95%

3-Methylbutenoic acid (541-47-9) → 4-bromo-3-(bromomethyl)but-2-enoic acid (75887-43-3)

Conditions	Yield
With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 4h; Heating;	95%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4h; Reflux;	95%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Reflux;	95%

3-Methylbutenoic acid (541-47-9) + 4-methoxy-phenol (150-76-5) → 4'-methoxyphenyl 3-methylbut-2-enoate (84346-76-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 6h; Ambient temperature;	95%
With aluminium trichloride; trichlorophosphate for 0.5h; Ambient temperature; Yield given;

3-Methylbutenoic acid (541-47-9) + rac-methylbenzylamine (618-36-0) → N-benzyl-3,3-dimethylacrylic amide (67264-80-6) + 3-Methyl-but-2-enoic acid (1-phenyl-ethyl)-amide (98379-81-8)

Conditions	Yield
With potassium hydroxide; bis(o-nitrophenyl)phenylphosphonate; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate other amines; multistep reaction;	A 95% B 85%

3-Methylbutenoic acid (541-47-9) + benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside (195006-98-5) → benzyl (R)-4,6-O-benzylidene-2-deoxy-2-(3-methyl-2-butenamido)-β-D-allopyranoside (434948-91-1)

Conditions	Yield
With trichloroacetic acid pentachlorophenyl ester; triethylamine In tetrahydrofuran at 20℃; for 8h;	95%

Upstream product

• 1823-52-5 4,4-dimethyloxetan-2-one 
• 609-12-1 ethyl 2-bromoisovalerate 
• 2033-24-1 cycl-isopropylidene malonate 
• 108-24-7 acetic anhydride 
• 101080-10-8 4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 504-20-1 phorone 
• 10323-40-7 2-bromoisovaleric acid 
• 124-41-4 sodium methylate 
• 29552-15-6 4-chloro-2-methylbut-3-yn-2-ol 
• 1617-31-8 3-methylbut-3-enoic acid 
• 5798-88-9 β-bromo-isovaleric acid 
• 625-08-1 3-Hydroxy-3-methylbutyric acid 
• 1518-06-5 1,3-dibromo-3-methyl-2-butanone 

Downstream Products

• 75974-47-9 α-bromo-β-methoxy-isovaleric acid 
• 5452-54-0 3-methyl-3-(3,4,5-trimethylphenyl)butanoic acid 
• 1010-48-6 3-methyl-3-phenylbutanoic acid 
• 220091-43-0 (3-methyl-crotonoyl)-(4-nitro-benzenesulfonyl)-amine 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 503-74-2 3-methylbutyric acid 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 556-82-1 3-methyl-2-buten-1-ol 
• 625-05-8 3-amino-3-methylbutanoic acid 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 1756-18-9 (2RS)-2,3-dihydroxy-3-methylbutanoic acid 
• 34876-10-3 3-methyl-2-butenoic anhydride 
• 1224-86-8 1,4-bis(1-carboxy-2-methylprop-2-yl)benzene 
• 21250-36-2 N-(4-methylphenyl)-3-methyl-2-butenamide 

Relevant articles and documents

Design, synthesis, and insecticidal activities of novel monohalovinylated pyrethroids

A series of novel monohalovinylated pyrethroids are designed and synthesized to replace one halo atom with a hydrogen atom on the double bond of dihalopyrethroids. Bioassays indicate that some of the synthesized compounds, such as 3j and 1j, exhibit high insecticidal activities against mosquitoes (Culex pipiens pallens), oriental armyworms (Mythimna separata), alfalfa aphids (Aphis medicagini), and carmine spider mites (Tetranychus cinnabarinus). Photolytic results of E-cis-1j suggest that monohalovinylated pyrethroids are photodegraded more easily than compound 12.

MANUFACTURING METHOD OF PENTYL ALCOHOL

A method for preparing methyl butenoic acid using (A) acetone is provided to economically mass-produce a pentyl alcohol economically. Reducing a (B)-methyl butenoic acid with a reducing agent. The present invention relates to a method for producing a pentyl alcohol comprising.

Synthesis and Exploration of Abscisic Acid Receptor Agonists Against Dought Stress by Adding Constraint to a Tetrahydroquinoline-Based Lead Structure

New oxotetrahydroquinolinyl- and oxindolinyl sulfonamides interacting with RCAR/(PYR/PYL) receptor proteins were identified as lead structures against drought stress in crops starting from protein docking studies of a sulfonamide lead structure, followed by in-depth SAR studies. Optimized five to six step synthetic approaches via substituted amino oxo-tetrahydro-quinolines and amino oxo-indolines as essential intermediates gave access to the envisaged oxo-tetrahydroquinolinyl and oxindolinyl sulfonamides. Whilst oxo-tetrahydroquinolinyl sulfonamides with additional carbon substituents or spiro-cycloalkyl groups exhibited only low to moderate target affinities, the corresponding spiro-oxindolinyl and oxo-tetrahydroquinolinyl sulfonamides carrying optimized N-substituents revealed strong interactions with RCAR/(PYR/PYL) receptor proteins in Arabidopsis thaliana. Remarkably, the in vitro activity observed for these new compounds was on the same level as observed for the naturally occurring plant hormone in line with strong efficacy against drought stress in-vivo (canola and wheat as broad-acre crops).

Quantitative production of butenes from biomass-derived γ-valerolactone catalysed by hetero-atomic MFI zeolite

The efficient production of light olefins from renewable biomass is a vital and challenging target to achieve future sustainable chemical processes. Here we report a hetero-atomic MFI-type zeolite (NbAlS-1), over which aqueous solutions of γ-valerolactone (GVL), obtained from biomass-derived carbohydrates, can be quantitatively converted into butenes with a yield of >99% at ambient pressure under continuous flow conditions. NbAlS-1 incorporates simultaneously niobium(v) and aluminium(iii) centres into the framework and thus has a desirable distribution of Lewis and Br?nsted acid sites with optimal strength. Synchrotron X-ray diffraction and absorption spectroscopy show that there is cooperativity between Nb(v) and the Br?nsted acid sites on the confined adsorption of GVL, whereas the catalytic mechanism for the conversion of the confined GVL into butenes is revealed by in situ inelastic neutron scattering, coupled with modelling. This study offers a prospect for the sustainable production of butene as a platform chemical for the manufacture of renewable materials.