109-49-9

Basic information

• Product Name: Allylacetone
• Synonyms: 1-Hexen-5-one;hex-5-;hex-5-en-2;TIMTEC-BB SBB009089;3-BUTEN-1-YL METHYL KETONE;ALLYLACETONE;5-HEXENE-2-ONE;5-HEXEN-2-ONE
• CAS NO: 109-49-9
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.14
• EINECS: 203-675-1
• Product Categories: Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 109-49-9.mol
• Article Data: 54

Chemical Properties

• Melting Point: -71.05°C (estimate)
• Boiling Point: 128-129 °C(lit.)
• Flash Point: 75 °F
• Appearance: Clear colorless liquid, typical ketone odor
• Density: 0.847 g/mL at 25 °C(lit.)
• Vapor Pressure: 10.1mmHg at 25°C
• Refractive Index: n20/D 1.419(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Soluble in water.
• BRN: 1699137
• CAS DataBase Reference: Allylacetone(CAS DataBase Reference)
• NIST Chemistry Reference: Allylacetone(109-49-9)
• EPA Substance Registry System: Allylacetone(109-49-9)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 109-49-9(Hazardous Substances Data)

Usage

Description

Allylacetone, also known as 4-(2-methyl-1-propenyl) phenol, is a chemical compound that is a clear colorless to light yellow liquid. It is an intermediate in pharmaceutical synthesis, perfumes, fungicides, insecticides, and fine chemicals.

Uses

Used in Pharmaceutical Industry:
Allylacetone is used as an intermediate in the synthesis of various pharmaceutical compounds.
Used in Perfume Industry:
Allylacetone is used as a natural identical flavor and fragrance in the perfume industry.
Used in Agrochemical Industry:
Allylacetone is used as an intermediate in the production of fungicides and insecticides.
Used in Fine Chemicals Industry:
Allylacetone is used as an intermediate in the production of fine chemicals.
Additionally, Allylacetone is also used to produce 2-methyl-hex-5-en-2-ol, which is a compound used in the synthesis of various chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2726, 1989 DOI: 10.1021/jo00272a050Tetrahedron Letters, 25, p. 5467, 1984 DOI: 10.1016/S0040-4039(01)81600-2

InChI:InChI=1/C6H10O/c1-3-4-5-6(2)7/h3H,1,4-5H2,2H3

Synthetic route

hex-5-en-2-one oxime (59239-06-4) → 1-hexen-5-one (109-49-9)

Conditions	Yield
Stage #1: hex-5-en-2-one oxime With 2,2'-dipyridyldiselenide; trimethylphosphane In tetrahydrofuran; toluene at 20℃; for 0.0333333h; Stage #2: With water In tetrahydrofuran at 20℃; for 0.5h; Further stages.;	97%
With tert.-butylhydroperoxide; dipyridinium dichromate In dichloromethane at 0℃; for 4h;	95%

2-acetyl-pent-4-enoic acid ethyl ester (610-89-9) → 1-hexen-5-one (109-49-9)

Conditions	Yield
With sodium hydroxide In water for 2h; Reflux;	80%

dichloromethane (75-09-2) + 1-(4-morpholinyl)-4-penten-1-one (58170-51-7) → 1-hexen-5-one (109-49-9)

Conditions	Yield
Stage #1: dichloromethane; 1-(4-morpholinyl)-4-penten-1-one With titanium tetrachloride; magnesium In tetrahydrofuran at 0℃; for 1.05h; Inert atmosphere; Stage #2: With water; potassium carbonate Inert atmosphere; chemoselective reaction;	80%

2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane (20449-21-2) → 1-hexen-5-one (109-49-9)

Conditions	Yield
With CuCl2*2H2O In acetonitrile for 0.5h; Ambient temperature;	74%

2-<(trimethylsilyl)oxy>-1,5-hexadiene (57711-32-7) → 1-hexen-5-one (109-49-9) + 1-chloro-5-hexen-2-one (73193-08-5)

Conditions	Yield
With copper dichloride In N,N-dimethyl-formamide 1) r.t., 3 h, 2) 50 deg C, 30 min;	A 20% B 68%
With copper dichloride In N,N-dimethyl-formamide 1) r.t., 3 h, 2) 50 deg C, 30 min; further reagent: FeCl3 in MeCN;	A 20% B 68%

2-bromo-2-nitrohex-5-ene (133367-87-0) → 1-hexen-5-one (109-49-9) + hex-5-en-2-ol (17397-24-9, 17397-29-4, 54774-27-5, 626-94-8) + 1-methyl-1-nitrocyclopentane (30168-50-4) + 2-nitrohex-5-ene (64999-95-7)

Conditions	Yield
2,2'-azobis(isobutyronitrile) In benzene at 40℃; Product distribution; Mechanism; Irradiation; different concentrations of Bu3SnH, without irradiation, absence of azobis(isobutyronitrile), presence of p-dinitrobenzene, presence of oxygen;	A n/a B n/a C n/a D 64%

1-diphenylphosphinoyl-4-(2-methyl-[1,3]dioxolan-2-yl)-propane (87109-17-9) → 2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane (20449-21-2) + 1-hexen-5-one (109-49-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 1h;	A 63% B 18%

3-chloroprop-1-ene (107-05-1) → 1-hexen-5-one (109-49-9)

Conditions	Yield
	63%

hex-5-en-2-ol (17397-24-9, 17397-29-4, 54774-27-5, 626-94-8) → 1-hexen-5-one (109-49-9)

Conditions	Yield
With [RuCl2(PPh3)2(2-PyCH21,3,5-triaza-7-phosphadamantane)].Br; potassium hydroxide In water for 48h; Schlenk technique; Reflux; Inert atmosphere;	56%
With chromic acid
With aluminum oxide; barium manganate; copper(II) sulfate In benzene for 10h; Ambient temperature;	78 % Chromat.
Multi-step reaction with 4 steps 1: 87 percent / pyridine / 1 h / Ambient temperature 2: 55 percent / lithium bromide / tetrahydrofuran / 6 h / Heating 3: 25 percent / sodium nitrite, urea / dimethylformamide / 48 h / Ambient temperature 4: 1.) NaOMe, 2.) potassium hexacyanoferrate(III) / 1.) methanol, 30 min, 2.) CH2Cl2, water, 10 min View Scheme

1,2-epoxy-5-hexene (10353-53-4) → 1-hexen-5-one (109-49-9) + 3-methylenecyclopentan-1-ol (21816-24-0)

Conditions	Yield
With Co(dimethylglyoximate)2(py)iPr; potassium tert-butylate In methanol at 34℃; for 24h; Inert atmosphere; Irradiation; regioselective reaction;	A 8 %Spectr. B 53%

2-methyl-3-oxa-1,5-hexadiene (7623-25-8) → 1-hexen-5-one (109-49-9)

Conditions	Yield
In benzene-d6 at 80 - 125.2℃; Rate constant; Thermodynamic data; activation (enthalpy and entropy);	45%
at 255℃;
With Chromosorb P Heating;

(Z)-3-Trimethylsilanyloxy-but-2-enoic acid allyl ester (114288-96-9) → 1-hexen-5-one (109-49-9) + α,α,α-triallyacetone (76003-04-8) + 3-allyl-hex-5-en-2-one (75265-80-4) + 3-allyl-2-octanone (102840-44-8)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 25 - 30℃; for 2h;	A 21% B 27% C 45% D 4%

allyl acetoacetate (1118-84-9) → 1-hexen-5-one (109-49-9) + 3-allyl-hex-5-en-2-one (75265-80-4)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 2h; Ambient temperature;	A 37% B 16 % Chromat.
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 2h; Ambient temperature;	A 37 % Chromat. B 16%
With palladium diacetate; triphenylphosphine In tetrahydrofuran for 0.5h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

acetonedicarboxylic acid (542-05-2) + Allyl acetate (591-87-7) → 1-hexen-5-one (109-49-9) + 3-allyl-hex-5-en-2-one (75265-80-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 0.5h; Ambient temperature;	A 31% B 45 % Chromat.
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 3h; Ambient temperature;	A 64 % Chromat. B 5%

Allyl acetate (591-87-7) + lithium acetoacetate (3483-11-2) → 1-hexen-5-one (109-49-9) + 3-allyl-hex-5-en-2-one (75265-80-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In benzene for 3h; Ambient temperature;	A 14% B 64 % Chromat.

hex-5-en-2-ol (17397-24-9, 17397-29-4, 54774-27-5, 626-94-8) → 1-hexen-5-one (109-49-9) + (S)-5-hexen-2-ol (626-94-8) + (2R)-hex-5-en-2-ol (17397-29-4)

Conditions	Yield
With D-glucose; Yarrowia lipolytica YL2; peptone In N,N-dimethyl-formamide at 28℃; for 96h; Oxidation; Microbiological reaction; Title compound not separated from byproducts;	A 6% B n/a C n/a

diphenylether (101-84-8) + allyl acetoacetate (1118-84-9) → 1-hexen-5-one (109-49-9)

Conditions	Yield
at 185 - 200℃;

2,2-bis-allyloxy-propane (35219-73-9) → 1-hexen-5-one (109-49-9) + 2-methyl-3-oxa-1,5-hexadiene (7623-25-8)

Conditions	Yield
With toluene-4-sulfonic acid

6-Bromo-2-hexanone (10226-29-6) → 1-hexen-5-one (109-49-9)

Conditions	Yield
With alkali

2-ethoxy-2-allyloxy-propane (87384-19-8) → 1-hexen-5-one (109-49-9) + 2-methyl-3-oxa-1,5-hexadiene (7623-25-8)

Conditions	Yield
With toluene-4-sulfonic acid

methyl-butyl-γ-butenyl-carbinol (861334-28-3) → 1-hexen-5-one (109-49-9)

Conditions	Yield
at 600℃;
at 600℃; beim Ueberleiten ueber Glaswolle;

allyl acetoacetate (1118-84-9) → 1-hexen-5-one (109-49-9)

Conditions	Yield
With diphenylether
tetrakis(polyethylenediphenylphosphine)palladium(0) In toluene at 100℃; for 0.0833333h;	100 % Chromat.
4Pd In toluene at 100℃; for 0.0833333h; Product distribution; other allylic esters of β-keto and β-cyano carboxylic acids;	100 % Chromat.

2,2-bis-allyloxy-propane (35219-73-9) + toluene-4-sulfonic acid (104-15-4) → 1-hexen-5-one (109-49-9) + 2-methyl-3-oxa-1,5-hexadiene (7623-25-8)

Conditions	Yield
bei langsamer Destillation;

chloroethylene (75-01-4) + ethyl acetate (141-78-6) → 1-hexen-5-one (109-49-9) + 3-Methyl-1,4-pentadien-3-ol (918-86-5)

Conditions	Yield
(i) Mg, THF, (ii) /BRN= 506104/, Et2O; Multistep reaction;

allyl bromide (106-95-6) + acetone (67-64-1) → 1-hexen-5-one (109-49-9)

Conditions	Yield
(i) nBu3SnOMe, Et2O, (ii) /BRN= 605308/; Multistep reaction;

1,5-Hexadien (592-42-7) → 1-hexen-5-one (109-49-9)

Conditions	Yield
With hydrogenchloride; p-nitrobenzenesulfonyl azide; hydroquinone 1.) benzene, 90 deg C, 7 d, protection from light; 2.) aq. ethanol, r. t., 24 h; Yield given. Multistep reaction;

Allyl ether (557-40-4) + N-isopropyliden-cyclohexyl amine (6407-36-9) → 1-hexen-5-one (109-49-9) + nona-1,8-dien-5-one (74912-33-7)

Conditions	Yield
With ethylmagnesium bromide Multistep reaction;

diallyl sulphide (592-88-1) + N-isopropyliden-cyclohexyl amine (6407-36-9) → 1-hexen-5-one (109-49-9) + nona-1,8-dien-5-one (74912-33-7)

Conditions	Yield
With ethylmagnesium bromide Multistep reaction;

Allyl acetate (591-87-7) + N-isopropyliden-cyclohexyl amine (6407-36-9) → 1-hexen-5-one (109-49-9) + nona-1,8-dien-5-one (74912-33-7)

Conditions	Yield
With ethylmagnesium bromide Multistep reaction;

1-hexen-5-one (109-49-9) → hex-5-en-2-ol (17397-24-9, 17397-29-4, 54774-27-5, 626-94-8)

Conditions	Yield
With potassium tert-butylate; hydrogen; RuHCl(PPh2CH2CH2NH2)2 at 20℃; under 2280 Torr; for 12h;	100%
With hydrogen; Ru((R,R)-cyP2N2)HCl In benzene-d6 at 20℃; under 2280.15 Torr; for 12h; Product distribution / selectivity; Alkaline conditions; Cooling with liquid nitrogen;	100%
With hydrogen; Ru((R,R)-cyP2(NH)2)HCl In benzene-d6 at 20℃; under 2280.15 Torr; for 12h; Product distribution / selectivity; Alkaline conditions; Cooling with liquid nitrogen;	100%

1-hexen-5-one (109-49-9) + hydrazine carboxamide (4426-72-6, 51433-48-8) → N-(hex-5-en-2-ylidene)semicarbazide (339207-38-4)

Conditions	Yield
With hydrogenchloride In methanol Reflux;	100%

1-hexen-5-one (109-49-9) + ethylene glycol (107-21-1) → 2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane (20449-21-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; for 2h; Dean-Stark; Schlenk technique; Inert atmosphere;	99%
With camphor-10-sulfonic acid; orthoformic acid triethyl ester In dichloromethane at 20℃; for 24h;	96%
	95%

1-hexen-5-one (109-49-9) + (E)-N-(2,6-dimethylphenyl)-2-phenyl-3H-3-iminoindole → (S,E)-1-(3-((2,6-dimethylphenyl)imino)-2-phenylindolin-2-yl)hex-5-en-2-one

Conditions	Yield
With L-proline In dimethyl sulfoxide at 20℃; for 168h; Mannich Aminomethylation; enantioselective reaction;	99%

1-hexen-5-one (109-49-9) + trisylhydrazine (39085-59-1) → hex-1-en-5-one 2,4,6-tri-isopropylbenzenesulphonyl hydrazone (64028-02-0)

Conditions	Yield
In tetrahydrofuran for 2h; Ambient temperature;	98%

1-hexen-5-one (109-49-9) → n-hexan-2-one (591-78-6)

Conditions	Yield
With [Ir(1-(1′-methylpyrazole)-3-(4′-methylphenyl)triazenide)Cp*Cl]; isopropyl alcohol at 90℃; for 1.33h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Inert atmosphere; Glovebox;	98%
With NaH-alkoxide-Ni salt reagent; water In tetrahydrofuran at 25℃; for 0.133333h;	90.5%
With hydrogen; [(C6Me6)2Ru2(PPh2)H2][BF4] In ethanol at 60℃; under 37503 Torr; for 24h;	85%

1-hexen-5-one (109-49-9) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → (E)-8,9-dimethyldeca-5,8-dien-2-one (1345734-98-6)

Conditions	Yield
With C35H38O5P2*Br2Co; zinc(II) iodide; zinc In dichloromethane at 20℃; Inert atmosphere; regioselective reaction;	98%

1-hexen-5-one (109-49-9) + Dimethylphenylsilane (766-77-8) → 6-(dimethyl(phenyl)silyl)hexan-2-one (52000-38-1)

Conditions	Yield
With platinum on carbon nanotubes In neat (no solvent) at 20℃; for 24h;	98%
With (bis(diisopropylphenyl-imidazol-2-ylidene)phenyl)CoN2 In benzene at 20℃; for 2h; chemoselective reaction;	97%
With triethyl borane; triisopropylsilanethiol In tetrahydrofuran at 20℃; regioselective reaction;	88%
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; N-ethyl-N,N-diisopropylamine; triisopropylsilanethiol In 1,4-dioxane at 20℃; Schlenk technique; Sealed tube; Inert atmosphere; Irradiation;	62%

1-hexen-5-one (109-49-9) + phenylmagnesium bromide (100-58-3) → 2-phenyl-5-hexen-2-ol (85924-68-1)

Conditions	Yield
In tetrahydrofuran at 0 - 22℃; for 1h; Inert atmosphere;	98%

1-hexen-5-one (109-49-9) + Selectfluor (140681-55-6) → C13H24ClFN2O(2+)*2BF4(1-)

Conditions	Yield
With cyclohexenone In acetonitrile for 12h; Inert atmosphere; Microwave irradiation;	98%

1-hexen-5-one (109-49-9) + phenylmethanethiol (100-53-8) → 6-(benzylthio)hexan-2-one

Conditions	Yield
With benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one In cyclohexane at 20℃; for 1h; Inert atmosphere; Sealed tube; Irradiation;	98%

methyl magnesium iodide (917-64-6) + 1-hexen-5-one (109-49-9) → 2-methylhex-5-en-2-ol (16744-89-1)

Conditions	Yield
In diethyl ether for 1h;	97%
	96%
In diethyl ether at 0 - 20℃;	91%

1-hexen-5-one (109-49-9) + (N,N-diethylamino)dimethylchlorosilane (6026-02-4) → N,N-diethyl-1-(hexa-1,5-dien-2-yloxy)-1,1-dimethylsilanamine (1190750-57-2)

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 20℃; for 1.25h; Inert atmosphere;	97%

1-hexen-5-one (109-49-9) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → C12H20O (1254327-41-7)

Conditions	Yield
With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane for 20h;	97%

1-hexen-5-one (109-49-9) + 4-methoxy-aniline (104-94-9) → C13H19NO (875540-94-6)

Conditions	Yield
With 2-Phenylbenzothiazolin; C51H59O4P In benzene at 20℃; for 48h; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	97%
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; 2-(3,5-dimethylphenyl)indoline In 1,3,5-trimethyl-benzene at 20 - 80℃; for 72h; Molecular sieve; Inert atmosphere; enantioselective reaction;	71%

1-hexen-5-one (109-49-9) + n-perfluorohexyl iodide (355-43-1) → 7,7,8,8,9,9,10,10,11,11,12,12,12-Tridecafluoro-5-iodo-dodecan-2-one (116486-79-4)

Conditions	Yield
With triethyl borane In hexane at 25℃; for 3.5h;	96%
With silver(I) acetate; tin(ll) chloride In methanol Ambient temperature;	94%
With diethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) dichloride In water at 20℃; for 3h; Kharasch reaction;	79%
With tin; silver(I) acetate In methanol for 24h; Ambient temperature;	67%
titanium tetrachloride; zinc In 1,2-dimethoxyethane at 75℃; for 24h;	15%

1-hexen-5-one (109-49-9) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)-1-methylpent-4-enylamine (54530-02-8)

Conditions	Yield
With formic acid; chloro-(pentamethylcyclopentadienyl)-{5-methoxy-2-{1-[(4-methoxyphenyl)imino-N]ethyl}phenyl-C}-iridium(lll); triethylamine In methanol at 80℃; for 1h; Inert atmosphere;	96%
With formic acid; triethylamine In methanol at 80℃; for 12h; Inert atmosphere;	93%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; S-benzyl isothiouronium chloride In toluene at 70℃; for 48h; Molecular sieve; Inert atmosphere;	92%

1-hexen-5-one (109-49-9) + 2-benzyl-2-methyl-3-morpholino-3-oxopropanal → 2-benzyl-2-methyl-1-morpholinononane-1,3,8-trione

Conditions	Yield
With [Rh(bis(dicylohexylphosphino)methane)(C6H5F)][BArF4] In acetone at 55℃; for 18h; Inert atmosphere; Sealed tube; regioselective reaction;	96%

1-hexen-5-one (109-49-9) → 5-hydroxy-6-iodo-hexan-2-one

Conditions	Yield
With N-iodo-succinimide In 1,2-dimethoxyethane; water at -20℃; for 2h; Addition; substitution;	95%
With iodine; bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 0 - 20℃;

1-hexen-5-one (109-49-9) + 4-dimethylamino-benzaldehyde (100-10-7) → 1-(4-dimethylaminophenyl)-2-propylbutane-1,3-dione (950587-57-2)

Conditions	Yield
[Ru(H)Cl(CO)(PPh3)3] In benzene for 5h; Heating;	95%

1-hexen-5-one (109-49-9) + ethyl 2-diethoxyphosphorylpropionate (3699-66-9) → ethyl (E,Z)-2,3-dimethyl-2,6-heptadienoate

Conditions	Yield
Stage #1: ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran; mineral oil Cooling with ice; Inert atmosphere; Stage #2: 5-Hexen-2-one In tetrahydrofuran; mineral oil at 20℃; for 72h; Inert atmosphere;	95%

1-hexen-5-one (109-49-9) + thioacetic acid (507-09-5) → S-(5-oxohexyl) ethanethioate (108419-94-9)

Conditions	Yield
With trifluoroacetic acid In chloroform at 66℃; for 4h;	95%

1-hexen-5-one (109-49-9) + thiophenol (108-98-5) → 6-Phenylsulfanyl-hexan-2-one (172419-22-6)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 80 - 90℃; for 5h;	94%

1-hexen-5-one (109-49-9) + 1,1,1,3,5,5,5-heptamethyltrisiloxan (1873-88-7) → C13H32O3Si3

Conditions	Yield
With (bis(diisopropylphenyl-imidazol-2-ylidene)phenyl)CoN2 In benzene at 20℃; for 5h; chemoselective reaction;	94%
Pt(0) N-heterocyclic carbene In xylene at 72℃; for 24h;	78%

nitroacetic acid ethyl ester (626-35-7) + 1-hexen-5-one (109-49-9) → ethyl 5-(3-oxobutyl)-4,5-dihydro-3-isoxazolecarboxylate (162739-96-0)

Conditions	Yield
With sodium hydroxide In water at 60℃; for 72h;	94%

1-hexen-5-one (109-49-9) + phenethylamine (64-04-0) → 1-(2-phenylethyl)-2,5-dimethyl-1H-pyrrole (50691-34-4)

Conditions	Yield
With palladium(II) trifluoroacetate; oxygen In toluene at 100℃; Wacker Oxidation;	94%

1-hexen-5-one (109-49-9) + 2,2-Diphenylethylamine (3963-62-0) → 1-(2,2-diphenylethyl)-2,5-dimethyl-1H-pyrrole (107112-44-7)

Conditions	Yield
With palladium(II) trifluoroacetate; oxygen In toluene at 100℃; Wacker Oxidation;	94%

1-hexen-5-one (109-49-9) + N-BOC-1,2-diaminoethane (57260-73-8) → tert-butyl (2-(2,5-dimethyl-1H-pyrrol-1-yl)ethyl)carbamate

Conditions	Yield
With palladium(II) trifluoroacetate; oxygen In toluene at 100℃; Wacker Oxidation;	94%

1-hexen-5-one (109-49-9) + ethylenediamine (107-15-3) → 1,2-bis(2,5-dimethyl-1H-pyrrol-1-yl)ethane (6306-70-3)

Conditions	Yield
With palladium(II) trifluoroacetate; oxygen In toluene at 100℃; Wacker Oxidation;	94%

Upstream product

• 35219-73-9 2,2-bis-allyloxy-propane 
• 1118-84-9 allyl acetoacetate 
• 61549-47-1 dec-5-ene-2,9-dione 
• 928-40-5 hexane-1,5-diol 
• 75-09-2 dichloromethane 
• 58170-51-7 1-(4-morpholinyl)-4-penten-1-one 
• 1101835-13-5 C₁₄H₂₀N₂O₄ 
• 107-05-1 3-chloroprop-1-ene 
• 50775-03-6 5-bromohex-5-en-2-one 
• 126-84-1 2,2-diethoxypropane 
• 87384-19-8 2-ethoxy-2-allyloxy-propane 
• 3695-29-2 5-iodo-2-pentanone 
• 3884-71-7 bromo-5-pentanone-2 
• 3695-28-1 5-iodo-2-pentanone ethylene ketal 

Downstream Products

• 123-76-2 levulinic acid 
• 101080-52-8 1-methyl-2-oxa-bicyclo[2.2.0]hexane 
• 2550-28-9 5-hexyn-2-one 
• 4160-75-2 1-cyclopropylpropan-2-one 
• 51024-76-1 (Z)-4-hexen-2-one 
• 763-92-8 (E)-4-hexen-2-one 
• 75-07-0 acetaldehyde 
• 156742-99-3 1-[(1S*,2S*)-2-(hydroxymethyl)cyclopropyl]ethanone 
• 393793-91-4 5-hydroxy-6-(phenylseleno)hexan-2-one 
• 2231-66-5 2,2-dimethyl-5-(propan-2-ylidene)-1,3-dioxane-4,6-dione 
• 54530-02-8 N-(4-methoxyphenyl)-1-methylpent-4-enylamine 
• 13141-45-2 (Z)-1,4-diphenylbut-1-ene-3-yne 
• 13343-79-8 (E)-1,4-Diphenylbut-1-en-3-yne 

Related news

Codimerization of Allylacetone (cas 109-49-9) with vinyl ketones catalyzed by [RhCl(C2H4)2]2 - SnCl208/19/2019

Codimerization of allylacetone with different vinyl ketones catalyzed by [RhCl (C2H4)2]2 - SnCl2 leads to the formation of 1,5- and 1,7-diketones.detailed

Relevant articles and documents

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FREE RADICAL CHAIN REACTION OF ALLYLIC TIN COMPOUNDS WITH ORGANIC HALIDES INVOLVING SH prime PROCESS.

Negatively substituted halomethanes were allylated easily by allyltin compounds via radical chain reaction involving S//H prime process. Aryl, aralkyl, and alkyl halides underwent similar chain reactions only when the tin compound was charged in excessive amounts.

Kinetic resolution of racemic secondary alcohols via oxidation with Yarrowia lipolytica strains

Cyclic and alicyclic racemic secondary alcohols are kinetically resolved via oxidation with Yarrowia lipolytica strains. The comparison of the oxidation reactions with the reductions of the corresponding ketones supports the hypothesis of the presence of

Polyethylene-Bound Soluble Recoverable Palladium(0) Catalysts

The use of diphenylphosphine-terminated ethylene oligomers as ligands for palladium(0) and palladium(II) is described.With use of these polymeric ligands, it is possible to carry out homogeneous reactions characteristic of (Ph3P)4Pd and (Ph3P)2Pd(OAc)2 with essentially complete recovery of the Pd catalyst.The only limitation to repeated reuse of the catalyst is its immolative catalytic oxidation of the phosphine ligand by adventitious oxygen.

PALLADIUM-CATALYZED REARRANGEMENT OF ALLYLIC ESTERS OF ACETOACETIC ACID TO GIVE γ,δ-UNSATURATED METHYL KETONES

Various allylic esters of acetoacetic acid undergo rearrangement to give γ,δ-unsaturated methyl ketones in high yields with elimination of carbon dioxide under mild conditions in the presence of catalytic amounts of Pd(OAc)2 and PPh3.

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An efficient method for deprotection of acetals

A variety of acetonides and acetals were efficiently cleaved using CuCl2.2H2O in MeCN. The method was effectively used in synthesis of chiral diols which are important in asymmetric synthesis.

Chromium-Catalyzed Production of Diols From Olefins

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

Synthesis of a Water-Soluble Ruthenium Complex and Its Catalytic Activity for Acceptorless Alcohol Dehydrogenation in Aqueous Medium

The synthesis of a ruthenium complex bearing a PN-chelating ligand is described. The complex, in the presence of KOH, enabled the synthesis of ketones from secondary alcohols in the absence of a hydrogen acceptor in aqueous medium. This synthetic protocol, which uses water as the medium, is green and has a high atom economy as it avoids the use of an acceptor and produces hydrogen as the sole byproduct. Mechanistic investigations revealed that the catalytic cycle involves a phosphine dissociative pathway.