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inquiry9-Decenoic acid, methyl ester Basic information Product Name: 9-Decenoic acid, methyl ester Synonyms: 9-Decenoic acid, methyl ester;methyl Sdecenoate CAS: 25601-41-
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9-Decenoic acid methyl ester Application:9-Decenoic acid methyl ester
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inquiryConditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 48h; Inert atmosphere; | 100% |
sulfuric acid for 4h; Heating; | 98% |
With sulfuric acid | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 23h; | 93% |
Conditions | Yield |
---|---|
With C50H60Br2MoN2O2 In pentane at 20℃; under 8625.86 Torr; for 12.5h; Reagent/catalyst; Concentration; Autoclave; Glovebox; | 86% |
With C29H47Cl2OPRu In carbonic acid dimethyl ester at 20℃; under 750.075 Torr; for 3h; Inert atmosphere; | |
With Hoveyda-Grubbs catalyst first generation In carbonic acid dimethyl ester at 20℃; under 750.075 Torr; for 3h; Inert atmosphere; |
10-(2-Nitro-phenylselanyl)-decanoic acid methyl ester
methyl 9-decenoate
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran for 15h; | 84% |
With dihydrogen peroxide In tetrahydrofuran for 24h; | 84% |
dimethyl (Z)-octadec-9-ene-1,18-dioate
acrylonitrile
A
methyl 9-decenoate
B
methyl 10-cyano-dec-9-enoate
Conditions | Yield |
---|---|
With Hoveyda-Grubbs catalyst second generation In toluene at 100℃; for 1h; Cross-metathesis; Inert atmosphere; | A n/a B 82% |
Conditions | Yield |
---|---|
Stage #1: Methyl oleate With tetraethylammonium iodide In toluene at 20℃; for 1h; Inert atmosphere; Glovebox; Stage #2: ethene With C50H59Br2Cl2N3O2SiW In toluene; benzene at 50℃; under 7600.51 Torr; for 18h; Reagent/catalyst; Concentration; Autoclave; Inert atmosphere; | 78% |
Grubbs catalyst first generation In dichloromethane at 40℃; under 7757.43 Torr; for 4h; Product distribution / selectivity; | |
1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene-dichloro(3-methyl-2-buteneylidene)-(tricyclohexylphosphine)ruthenium In dichloromethane at 40 - 60℃; under 7757.43 Torr; for 2 - 4h; Product distribution / selectivity; |
octadec-9-enoic acid methyl ester
ethene
A
1-Decene
B
methyl 9-decenoate
C
9-octadecene
D
dimethyl 9-octadecen-1,18-dioate
Conditions | Yield |
---|---|
With dichloro[(2-(tert-butyl)-6-propylphenoxy)(pyrrolidin-1-ium-1-ylidene)methanide](2-isopropoxyphenylmethylene)ruthenium(II) at 40℃; under 7757.43 Torr; Reagent/catalyst; | A 73% B n/a C n/a D n/a |
With RuCl2(CN2C2H4(C6H3(CH(CH3)2)2)(C7H8(CH3)3))(CHC6H4OCH(CH3)2) In dichloromethane at 40℃; under 7757.43 Torr; for 6h; Inert atmosphere; | |
Stage #1: octadec-9-enoic acid methyl ester; ethene With [1 ,3-bis-(2,4,6-trimethylpheuyl)-2-imidazolidinylidene]dichloro(phenylindenylidene)(acetonitrile)ruthenium(II) at 40℃; under 8517.48 Torr; for 4h; Glovebox; Sealed tube; Inert atmosphere; Stage #2: With tris(hydroxymethyl)phosphine In isopropyl alcohol at 70℃; for 1h; Catalytic behavior; | |
With Grubbs catalyst first generation In toluene for 0.333333h; Reagent/catalyst; Flow reactor; |
Conditions | Yield |
---|---|
Stage #1: methanol; (2-nitrophenyl)(undec-10-en-1-yl)selane With ozone; sodium hydroxide In dichloromethane at -78℃; Stage #2: With oxygen In dichloromethane at -78℃; Stage #3: In dichloromethane at -78 - 20℃; | 65% |
octadec-9-enoic acid methyl ester
ethene
A
1-Decene
B
methyl 9-decenoate
Conditions | Yield |
---|---|
With F6P(1-)*C48H51Br2Cl2N4O2W(1+) | A n/a B 62% |
silica gel In dichloromethane under 5250.4 Torr; for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With Grubbs catalyst first generation In toluene for 0.333333h; Flow reactor; |
methyl (9E)-octadec-9-enoate
but-3-enenitrile
A
methyl 9-decenoate
B
methyl 11-cyano-9-undecenoate
Conditions | Yield |
---|---|
With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In chlorobenzene for 7h; | A 9.2 %Chromat. B 55% |
Methyl oleate
ethene
A
1-Decene
B
methyl 9-decenoate
C
9-octadecene
D
dimethyl 9-octadecen-1,18-dioate
Conditions | Yield |
---|---|
Cl2(PCy3)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC6H5 at 20℃; for 12h; Product distribution / selectivity; | A 43% B 46% C 3% D 2% |
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 20 - 23℃; under 11103.3 - 26618.1 Torr; Autoclave; Inert atmosphere; | |
With BerEt In toluene at 40℃; under 3102.97 Torr; for 1h; microfluidic reactor; |
octadec-9-enoic acid methyl ester
ethene
A
1-Decene
B
methyl 9-decenoate
C
dimethyl 9-octadecen-1,18-dioate
Conditions | Yield |
---|---|
With C29H47Cl2OPRu In carbonic acid dimethyl ester at 20℃; under 750.075 Torr; Inert atmosphere; | A 42% B 43% C 2% |
Conditions | Yield |
---|---|
With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In chlorobenzene at 110℃; for 4h; | A 16.2 %Chromat. B 42.9% |
undecanedioic acid monomethyl ester
methyl 9-decenoate
Conditions | Yield |
---|---|
With pyridine; lead(IV) acetate; copper diacetate In benzene for 3h; Heating; | 36.3% |
Conditions | Yield |
---|---|
Multistep reaction; |
1-butylene
octadec-9-enoic acid methyl ester
A
1-Decene
B
methyl 9-decenoate
C
dodec-3-ene
D
9-dodecenoic acid methyl ester
Conditions | Yield |
---|---|
With tetramethylstannane; tungsten(VI) chloride at 20 - 100℃; Kinetics; Product distribution; Mechanism; |
1-Heptene
octadec-9-enoic acid methyl ester
A
1-Decene
B
methyl 9-decenoate
C
6-pentadecene
Conditions | Yield |
---|---|
With tetramethylstannane; tungsten(VI) chloride at 20 - 100℃; Kinetics; Product distribution; Mechanism; |
1-hexene
octadec-9-enoic acid methyl ester
A
1-Decene
B
methyl 9-decenoate
C
myristelaidic acid methyl ester
D
1-tetradecene
Conditions | Yield |
---|---|
With tetramethylstannane; tungsten(VI) chloride at 20 - 100℃; Kinetics; Product distribution; Mechanism; |
Methyl oleate
ethene
A
trans-9-octadecene
B
Dimethyl (E)-octadec-9-enedioate
C
1-Decene
D
methyl 9-decenoate
Conditions | Yield |
---|---|
aluminum oxide; tetramethylstannane; rhenium(VII) oxide In chlorobenzene at 19.9℃; under 1500.1 Torr; for 20h; Product distribution; var. of catalyst, ratio substrate : catalyst, solvent, temp., pressure; |
10-bromodecanoic acid methyl ester
methyl 9-decenoate
Conditions | Yield |
---|---|
With sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; dihydrogen peroxide 1) EtOH, THF, 8h, RT 2) 6h, RT; Yield given. Multistep reaction; | |
Multi-step reaction with 3 steps 1: 1.) aq. NaOH / 1.) 50 deg C 2: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 3: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme | |
Multi-step reaction with 3 steps 1: 1.) 20percent KOH / 1.) water, 50 deg C 2: 78 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 3: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme | |
Multi-step reaction with 2 steps 1: 76 percent / NaBH4 / ethanol / 13 h / Ambient temperature 2: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme |
methyl 9-decenoate
Conditions | Yield |
---|---|
With hydrogenchloride; zinc |
Conditions | Yield |
---|---|
Grubbs catalyst first generation In dichloromethane at 50℃; under 7500.6 Torr; for 2h; metathesis; | |
phoban-indenylidene ruhenium catalyst at 50℃; for 2h; Product distribution; Further Variations:; Catalysts; | |
Grubbs catalyst first generation In toluene at 30℃; under 3102.97 Torr; for 4h; | A 19.9 %Chromat. B 18 %Chromat. |
(9Z,11E)-methyl octadeca-9,11-dienoate
ethene
A
deca-1,3-diene
B
oct-1-ene
C
methyl 9-decenoate
D
tetradec-7-ene
E
methyl dodeca-9,11-dienoate
F
dimethyl 9-octadecen-1,18-dioate
Conditions | Yield |
---|---|
RuCl2(sIMes)(CHPh)(pyridine)2 In dichloromethane at 30℃; under 7757.43 Torr; for 0.5 - 17.45h; Product distribution / selectivity; | |
Mol's catalyst In dichloromethane at 30℃; under 7757.43 Torr; for 0.5 - 17.45h; Product distribution / selectivity; | |
C34H44Cl2N2ORu In dichloromethane at 30℃; under 7757.43 Torr; for 0.5 - 17.45h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
In methanol; hexane; benzene at 25℃; for 0.5h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / CrO3; H2SO4 / acetone 2: 98 percent / H2SO4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1.) 48 percent HBr, concd. H2SO4; 2.) KMnO4 / 1.) 3 h, reflux; 2.) 20percent H2SO4, 15-20 deg C 3: 1.) aq. NaOH / 1.) 50 deg C 4: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 5: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme | |
Multi-step reaction with 4 steps 2: 1.) 20percent KOH / 1.) water, 50 deg C 3: 78 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 4: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme | |
Multi-step reaction with 3 steps 2: 76 percent / NaBH4 / ethanol / 13 h / Ambient temperature 3: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme |
10-bromodecanoic acid
methyl 9-decenoate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: 1.) aq. NaOH / 1.) 50 deg C 3: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 4: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme | |
Multi-step reaction with 2 steps 1: 94 percent / TsOH / 24 h / Ambient temperature 2: 1) o-Nitrophenyl selenocyanate, NaBH4 2) 30percent H2O2 / 1) EtOH, THF, 8h, RT 2) 6h, RT View Scheme |
methyl 10-hydroxydecanoate
methyl 9-decenoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / tributylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 2: 84 percent / aq. H2O2 / tetrahydrofuran / 24 h View Scheme | |
Multi-step reaction with 2 steps 1: 78 percent / tri-n-butylphosphine / tetrahydrofuran / 0.5 h / Ambient temperature 2: 84 percent / 30percent H2O2 / tetrahydrofuran / 15 h View Scheme |
Methyl 10-undecenoate
methyl 9-decenoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) BF3*THF, 2) Jones' reagent / 1a) 0 deg C, 2 h, b) r.t., 2 h, 2) acetone, r.t., 3 h 2: 36.3 percent / Pb(OAc)4, pyridine, Cu(OAc)2 / benzene / 3 h / Heating View Scheme |
9-Decen-1-ol
methyl 9-decenoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / CrO3 / acetone; aq. H2SO4 / 20 h / Ambient temperature 2: 1.) SOCl2 / 1.) methylene dichloride, 4.0 h reflux; 2.) room temp., 2.0 h View Scheme | |
Multi-step reaction with 2 steps 1: chromium(VI) oxide; sulfuric acid / acetone / 0.25 h / 0 °C 2: diethyl ether View Scheme |
methyl 9-decenoate
9-Decen-1-ol
Conditions | Yield |
---|---|
Stage #1: methyl 9-decenoate With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5.5h; Cooling; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; Reagent/catalyst; Concentration; Solvent; Temperature; Time; | 98.3% |
With lithium aluminium tetrahydride In tetrahydrofuran at 15 - 20℃; for 5.5h; Inert atmosphere; | 98.3% |
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 15 - 20℃; for 2h; Sealed tube; Cooling with ice; Inert atmosphere; | 97.14% |
Conditions | Yield |
---|---|
Stage #1: methyl 9-decenoate; 2,2'-iminobis[ethanol] at 100℃; for 5h; Inert atmosphere; Stage #2: With sodium methylate In methanol | 98% |
methyl 9-decenoate
methyl E-8-decenoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 10h; Heating; | 97% |
With toluene-4-sulfonic acid |
methyl 9-decenoate
dec-9-enoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In water; isopropyl alcohol at 20 - 54℃; under 760.051 Torr; for 4.5h; Inert atmosphere; Large scale; | 97% |
With potassium hydroxide In tetrahydrofuran; water for 14h; Ambient temperature; | 90% |
Stage #1: methyl 9-decenoate With potassium hydroxide In glycerol at 100 - 140℃; Stage #2: With sulfuric acid In water; glycerol at 90℃; | |
With water; sodium hydroxide at 50℃; for 1h; | 26.3 g |
With water; potassium hydroxide In isopropyl alcohol at 30 - 55℃; for 4h; | 957 g |
methyl 9-decenoate
Conditions | Yield |
---|---|
With potassium osmate(VI) dihydrate; potassium hexacyanoferrate(III); sodium hydrogencarbonate; potassium carbonate; hydroquinine (anthraquinone-1,4-diyl) diether In water; tert-butyl alcohol at -20℃; for 48h; Sharpless asymmetric dihydroxylation; | 97% |
Conditions | Yield |
---|---|
Stage #1: methyl 9-decenoate; ethanolamine at 110℃; for 6h; Inert atmosphere; Stage #2: With potassium hydroxide In methanol | 97% |
methyl 9-decenoate
methyl 8-(oxiran-2-yl)octanoate
Conditions | Yield |
---|---|
With ethylbenzene hydroperoxide; molybdenum naphthenate In ethylbenzene at 200℃; for 3.5h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 96.4% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1h; | 86.4% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Cooling with ice; |
methyl 9-decenoate
Conditions | Yield |
---|---|
With tributyl-amine; titanium tetrachloride In toluene at 0 - 5℃; for 1h; Condensation; | 93% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate In dichloromethane at 40℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction; | 91% |
methyl 9-decenoate
(E)-1,4-hexadiene
(9Z,12E)-9,12-Tetradecadiensaeure-methylester
Conditions | Yield |
---|---|
With C35H47N3O4Ru In tetrahydrofuran at 20℃; for 5h; Glovebox; Inert atmosphere; chemoselective reaction; | 82% |
methyl 9-decenoate
dimethyl 9-octadecen-1,18-dioate
Conditions | Yield |
---|---|
With Mo(N-2,6-’Pr2-C5H3)(CHCMe2Ph)(2,5-dimeth-ylpyrrolide)(O-2,6-Ph2C5H3) at 50℃; Reagent/catalyst; Temperature; Inert atmosphere; Molecular sieve; Glovebox; | 80.9% |
With [1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene][2-isopropoxy-5-(2,2,2-trifluoroacetamido)benzylidene]ruthenium(II) dichloride In toluene at 110℃; for 2h; Inert atmosphere; | 63% |
Grubbs catalyst first generation at 50℃; under 3.7503 Torr; for 2h; |
Conditions | Yield |
---|---|
With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In dichloromethane for 3.5h; Reflux; | 79% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In 1,2-dichloro-ethane at 60℃; for 4h; Suzuki-Miyaura Coupling; | 77% |
methyl 9-decenoate
1-bromo-2-(triisopropylsilyl)acetylene
Conditions | Yield |
---|---|
With silver tetrafluoroborate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium acetate at 60℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube; Overall yield = 45 percent; Overall yield = 25.2 mg; regioselective reaction; | A n/a B 75% |
methyl 9-decenoate
methyl ester of azelaic acid aldehyde
Conditions | Yield |
---|---|
Stage #1: methyl 9-decenoate With ozone In dichloromethane at -78℃; Stage #2: With acetic acid; zinc Further stages.; | 72% |
Stage #1: methyl 9-decenoate With oxygen; ozone; acetic acid for 7h; Cooling with water bath; Industry scale; Stage #2: With zinc In diethyl ether; water Product distribution / selectivity; Industry scale; | |
Multi-step reaction with 2 steps 1: ozone / dichloromethane / -78 °C / Inert atmosphere 2: dimethylsulfide / 20 °C / Inert atmosphere View Scheme | |
With potassium osmate(VI) dihydrate; sodium periodate In tetrahydrofuran; water for 5h; |
methyl 9-decenoate
di(4-tosyl)amine
methyl 10,11-bis(4-methyl-N-tosylphenylsulfonamido)undecanoate
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene In dichloromethane at 50℃; for 12h; | 70% |
Conditions | Yield |
---|---|
Stage #1: methyl 9-decenoate; carbon monoxide With hydrogen; 1,1'-[2,7-bis(1,1-dimethylethyl)-9,9-dimethyl-9H-xanthene-4,5-diyl]bis[1,1-diphenylphosphine]; Rh(acac)(CO)2 at 20 - 100℃; under 23272.3 Torr; for 20h; Stage #2: 5 % platinum on carbon In 1,4-dioxane at 150℃; under 25858.1 Torr; for 20h; | 65% |
methyl 9-decenoate
(S)-dec-9-en-2-ol
(S,Z)-methyl 17-hydroxyoctadece-9-enoate
Conditions | Yield |
---|---|
With C35H47N3O4Ru In dichloromethane at 20℃; for 24h; Inert atmosphere; diastereoselective reaction; | 59% |
methyl 9-decenoate
Conditions | Yield |
---|---|
With C35H47N3O4Ru In dichloromethane at 60℃; Catalytic behavior; Reagent/catalyst; Temperature; Cross Metathesis; Sealed tube; | 59% |
With C35H47N3O4Ru In dichloromethane at 60℃; Catalytic behavior; Reagent/catalyst; Temperature; Cross Metathesis; Sealed tube; | 43% |
With C35H47N3O4Ru In dichloromethane at 60℃; Catalytic behavior; Reagent/catalyst; Temperature; Cross Metathesis; Sealed tube; | 40% |
methyl 9-decenoate
2,4,6,8-tetramethylcyclotetrasiloxane
Conditions | Yield |
---|---|
Stage #1: methyl 9-decenoate With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 20℃; for 0.0833333h; Stage #2: 2,4,6,8-tetramethylcyclotetrasiloxane In toluene for 2h; Reflux; | 58% |
In ethyl acetate; toluene |
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