765-43-5

Basic information

• Product Name: 1-Cyclopropylethan-1-One
• Synonyms: ACETYLCYCLOPROPANE;ACETYLTRIMETHYLENE;AKOS BBS-00004282;1-CYCLOPROPYL-1-ETHANONE;1-CYCLOPROPYL-ETHANONE;CPMK;CYCLOPROPYL METHYL KETONE;METHYL CYCLOPROPYL KETONE
• CAS NO: 765-43-5
• Molecular Formula: C₅H₈O
• Molecular Weight: 84.12
• EINECS: 212-146-4
• Product Categories: Pharmaceutical Intermediates;Miscellaneous;ketone;API intermediates;Cyclopropanes;Simple 3-Membered Ring Compounds;Cycloalkanes
• Mol File: 765-43-5.mol

Chemical Properties

• Melting Point: <-70°C
• Boiling Point: 114 °C(lit.)
• Flash Point: 70 °F
• Appearance: Clear colorless to very slightly yellow/Liquid
• Density: 0.849 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: Flammables area
• Solubility: 185g/l
• Explosive Limit: 1.7%(V)
• Water Solubility: Fully miscible in water.
• BRN: 1633817
• CAS DataBase Reference: 1-Cyclopropylethan-1-One(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclopropylethan-1-One(765-43-5)
• EPA Substance Registry System: 1-Cyclopropylethan-1-One(765-43-5)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 9-16-29-33
• RIDADR: UN 1224 3/PG 2
• WGK Germany: 3
• RTECS: KM5648000
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 765-43-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to very slightly yellow liquid

Uses

Cyclopropyl methyl ketone was used in the preparation of homoallylic alcohols. Acetylcyclopropane is used as an intermediate for the manufacturing pharmaceuticals, agrochemicals and other organic compounds.

InChI:InChI=1/C5H8O/c1-4(6)5-2-3-5/h5H,2-3H2,1H3

Synthetic route

1-cyclopropylethanol (765-42-4) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With acetic acid; 1,1'-(phenyl-l3-iodanediyl)bis(pyridinium)trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; Inert atmosphere; Molecular sieve; chemoselective reaction;	99%
With trifluorormethanesulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In 1,4-dioxane at 20℃; for 0.25h;	98%
With manganese (VII)-oxide In tetrachloromethane; acetone at -70℃;	92%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With sodium iodide at 192℃; under 4500.45 Torr; Reagent/catalyst; Temperature; Pressure;	97.12%
Stage #1: 3-acetyl-2-oxo-4,5-dihydrofuran With hydrogenchloride In water at 100℃; for 2h; Stage #2: With sodium hydroxide In water at 80 - 100℃; for 2h;	90.2%
With 1-methyl-pyrrolidin-2-one; sodium iodide at 170℃; for 3h;	59%

methyl vinyl ketone (78-94-4) + 1,2-dibromomethane (74-95-3) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With sodium iodide; nickel dibromide; zinc In tetrahydrofuran at 0℃; for 96h;	97%

2,5-dichloro-2-pentene (20177-02-0) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With sulfuric acid at 40 - 45℃; for 2h;	95.2%

3-diphenylphosphinoyl-5-hydroxypentan-2-one (89625-16-1) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 30℃; for 2h;	95%
With potassium tert-butylate In tert-butyl alcohol for 2h;	81%

5-chloro-2-pentanone (5891-21-4) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide at 90 - 100℃; for 1.5h; Reagent/catalyst; Temperature;	88.04%
With potassium hydroxide Versetzen mit Wasser und anschliessend Erhitzen;
With sodium hydroxide; water Versetzen mit Wasser und anschliessend Erhitzen;

Cyclopropylacetylene (6746-94-7) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water In methanol at 110℃; for 6h;	86%
With 3,4,5-trihydroxybenzoic acid; water at 60℃; for 6h; Sealed tube; Green chemistry;	75%
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I) In methanol; water at 110℃; for 6h; Schlenk technique; regioselective reaction;	> 99 %Spectr.
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water; silver trifluoromethanesulfonate In methanol at 120℃; for 6h;

acetoacetic acid methyl ester (105-45-3) + ethylene dibromide (106-93-4) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
Stage #1: acetoacetic acid methyl ester; ethylene dibromide With sodium hydride at 55℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 60℃; for 2h; pH=8 - 9;	84%

ethenylcyclopropane (693-86-7) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With oxygen; copper(l) chloride; palladium dichloride In water; N,N-dimethyl-formamide at 40℃; for 6h;	80%

cyclopropylmethyl ketone 2,4-dinitrophenylhydrazone (790-13-6) → Cyclopropyl methyl ketone (765-43-5) + benzene-1,2,4-triamine (615-71-4)

Conditions	Yield
With vanadium(II) chloride In tetrahydrofuran for 1h; Heating;	A 74% B n/a

2-Methyl-4,5-dihydrofuran (1487-15-6) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With sulfonic acid resin at 50℃; for 2h; Reagent/catalyst; Temperature;	68.8%
at 430℃; for 0.005h; degree of conversion, other temperatures and reaction times;
at 710 - 760℃; Thermodynamic data; E(excit.), isomerization;

methyllithium (917-54-4) + cyclopropanecarboxylic acid (1759-53-1) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
In diethyl ether 1.) 0 deg C; 2.) 2 h, reflux;	63%

cyclopropyl methyl ketone oxime (51761-72-9) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With triethylammonium chlorochromate(VI) In 1,2-dichloro-ethane for 2h;	61%

cyclopropyltrimethylsilane (930-40-5) + acetyl chloride (75-36-5) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With aluminium trichloride In dichloromethane 0 deg C to reflux;	60%

3, 5-dichloro-2-pentanone (58371-98-5) → 5-chloro-2-pentanone (5891-21-4) + Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With tetraethylammonium tosylate In dimethyl sulfoxide electrolysis;	A 36% B 51%

(C4H9)3SnOCH(CH3)C3H5 (33866-86-3) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With Bromotrichloromethane	50%
With CCl3Br	50%
With t-C4H9OOC4H9-t byproducts: C3H7COCH3;
With t-C4H9OOC4H9-t byproducts: C3H7COCH3;

5-Hydroxy-2-pentanone (1071-73-4) → 2-Methyl-4,5-dihydrofuran (1487-15-6) + pent-4-en-2-one (13891-87-7) + Cyclopropyl methyl ketone (765-43-5) + acetaldehyde (75-07-0) + 2-Pentanone (107-87-9) + acetone (67-64-1)

Conditions	Yield
at 550℃; for 0.005h; Product distribution; 400 - 500 deg C;	A 6.7% B 43% C 15% D 2.41% E 9% F 10.8%

1-phenyl-1-cyclopropylmethanol (1007-03-0) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With oxygen In hexane at 68.84℃; under 750.075 Torr; for 24h; Molecular sieve;	42%

cyclopropylmethyl-methyl-amine hydrochloride + sodium pyruvate (113-24-6) → Cyclopropyl methyl ketone (765-43-5) + L-alanin (56-41-7) + (R)-1-cyclopropylethylamine sulfate

Conditions	Yield
Stage #1: cyclopropylmethyl-methyl-amine hydrochloride; sodium pyruvate With hydrogenchloride; sodium hydroxide; air; phosphoric acid In water at 28℃; for 46h; pH=8; aq. phosphate buffer; Microbiological reaction; Resolution of racemate; Stage #2: With sulfuric acid In water optical yield given as %ee;	A n/a B n/a C 34.2%

5-iodo-2-pentanone (3695-29-2) → Cyclopropyl methyl ketone (765-43-5) + 1-Brom-5-iod-2-methyl-1-penten

Conditions	Yield
With piperidine; n-butyllithium; bromo(bromomethyl)triphenylphosphorane In diethyl ether; hexane for 12h; Heating;	A 31% B 9%

oxirane (75-21-8) + (Acetylmethylen)tri(n-butyl)phosphoran (39743-80-1) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
at 150℃; for 15h;	30%

acetic acid (64-19-7) + cyclopropanecarboxylic acid (1759-53-1) → 4-butanolide (96-48-0) + Cyclopropyl methyl ketone (765-43-5) + acetone (67-64-1)

Conditions	Yield
catalyst B at 360℃; for 2 - 30.17h;	A 1.05% B 2.39% C 2.46%
catalyst A at 360℃; for 2 - 24h;	A 0.58% B 0.74% C 0.41%

2-Methyl-4,5-dihydrofuran (1487-15-6) → 3-penten-2-one (625-33-2) + Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
at 525℃; Erhitzen;

bromo-5-pentanone-2 (3884-71-7) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With potassium carbonate
With potassium hydroxide
With potassium hydroxide
With diphenylmercury(II) In toluene Heating;

isopropenylcyclopropane (4663-22-3) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
With potassium permanganate

1-Acetylcyclopropane-1-carboxylic acid (56172-71-5) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
at 200℃;

methylmagnesium bromide (75-16-1) + cyclopropropanecarbonitrile (5500-21-0) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
Behandeln des Reaktionsprodukts mit Wasser;

methyl magnesium (1+); bromide + cyclopropropanecarbonitrile (5500-21-0) → Cyclopropyl methyl ketone (765-43-5)

Conditions	Yield
analog verlaeuft die Reaktion mit β-Campholensaeurenitril, Zimtsaeurenitril und α.β-Diphenyl-n-valeronitril;

1-chloro-1-cyclopropylethene (24154-06-1) → Cyclopropyl methyl ketone (765-43-5) + Cyclopropylacetylene (6746-94-7)

Conditions	Yield
With silver perchlorate In acetic acid

2,2-dimethyltetrahydrofuran (1003-17-4) + 1-Cyclopropyl-ethylidene-oxonium (70058-20-7) → Cyclopropyl methyl ketone (765-43-5) + 2,2-Dimethyl-tetrahydro-furanium (878559-53-6)

Conditions	Yield
at 24.9℃; Thermodynamic data; ΔG0;

Cyclopropyl methyl ketone (765-43-5) + trimethylsilylacetylene (1066-54-2) → 2-cyclopropyl-4-trimethylsilanyl-but-3-yn-2-ol

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In hexanes; diethyl ether at -78℃; for 1.16667h; Stage #2: Cyclopropyl methyl ketone In hexanes; diethyl ether at 20℃; for 48h;	100%
With methyllithium 1.) ether, room temperature, 2 h; Multistep reaction;

4-Trifluoromethylbenzaldehyde (455-19-6) + Cyclopropyl methyl ketone (765-43-5) → (E)-1-cyclopropyl-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one (72881-74-4)

Conditions	Yield
With sodium methylate In methanol at 23℃; for 16h;	100%
With sodium hydroxide In ethanol; water at 60℃;	91%

Cyclopropyl methyl ketone (765-43-5) + formic acid ethyl ester (109-94-4) → potassium 3-cyclopropyl-3-oxoprop-1-en-1-olate

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃;	100%

Cyclopropyl methyl ketone (765-43-5) + ethyl 2-cyanoacetate (105-56-6) → (E,Z)-ethyl 2-cyano-3-cyclopropyl-2-butenoate (17407-28-2)

Conditions	Yield
	99.5%
	29%
With ammonium acetate; acetic acid In benzene

Cyclopropyl methyl ketone (765-43-5) → 5-iodo-2-pentanone (3695-29-2)

Conditions	Yield
With diiodosilane In dichloromethane at -42℃; for 0.0833333h;	99.5%
With diphosphorus tetraiodide In acetone at 20℃; for 1.5h;	88%
With trimethylsilyl iodide In tetrachloromethane 1.) -20 deg C, 0.5 h, 2.) 25 deg C, 2 h;	85%
With pyridine hydroiodide; tetra-(n-butyl)ammonium iodide In acetonitrile for 4h; Heating;	5%
With trimethylsilyl iodide In tetrachloromethane at -20℃; for 0.5h; Product distribution; var. cyclopropyl ketones; other temp., time;

Cyclopropyl methyl ketone (765-43-5) + (2,4,6-trichlorophenyl)hydrazine (5329-12-4) → 1-cyclopropylethanone 2,4,6-trichlorophenylhydrazone

Conditions	Yield
With acetic acid In ethanol for 8h; Heating;	99%

Cyclopropyl methyl ketone (765-43-5) → 2-bromo-1-cyclopropylethan-1-one (69267-75-0)

Conditions	Yield
With bromine In methanol at -5℃; for 2h;	99%
With bromine In methanol at 0 - 20℃; for 1.5h;	99%
With bromine In methanol at 25℃; for 16h;	98%

Cyclopropyl methyl ketone (765-43-5) → (R)-1-cyclopropylethanol (6516-09-2) + (S)-1-methyl-1-cyclopropylmethanol (55637-37-1)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (SC,SC,RFC)-1-(diphenylphosphino)-2-[1-N-((4S)-4-tert-butyl-2-oxazolinyl-2-ylmethyl)ethyl]ferrocene; hydrogen; potassium carbonate In isopropyl alcohol at 25℃; under 15201 Torr; for 2h; Glovebox; Autoclave; enantioselective reaction;	A 99% B n/a
With sodium hydroxide; 3-pinanyl-9-borabicyclo[3.3.1]nonane; dihydrogen peroxide 1.) 6000 atm, 25 deg C, 5.5 days, 2.) THF, 60 deg C, 4 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With 3-pinanyl-9-borabicyclo[3.3.1]nonane under 4560000 Torr; for 132h; Yield given. Title compound not separated from byproducts;

Cyclopropyl methyl ketone (765-43-5) + N,N-dimethyl acetamide (127-19-5) → 2-cyclopropyl-2-oxoethyl acetate (89898-26-0)

Conditions	Yield
Stage #1: Cyclopropyl methyl ketone; N,N-dimethyl acetamide With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h; Stage #2: With water for 0.166667h; Further stages.;	99%

Cyclopropyl methyl ketone (765-43-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Formic acid 2-cyclopropyl-2-oxo-ethyl ester (357943-56-7)

Conditions	Yield
Stage #1: Cyclopropyl methyl ketone; N,N-dimethyl-formamide With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h; Stage #2: With water for 0.166667h; Further stages.;	99%

methanol (67-56-1) + Cyclopropyl methyl ketone (765-43-5) → 5-methoxy-2-pentanone (17429-04-8)

Conditions	Yield
With copper(ll) bromide In water at 180℃; for 6h;	99%

Cyclopropyl methyl ketone (765-43-5) + methyl cyclopropylcarboxylate (2868-37-3) → 1,3-dicyclopropyl-1,3-propanedione (30923-64-9)

Conditions	Yield
Stage #1: Cyclopropyl methyl ketone; methyl cyclopropylcarboxylate With ethanol; sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With 18-crown-6 ether at 40℃; for 3h;	99%
With sodium methylate In dimethyl sulfoxide at 55℃; for 8h;	78%
With sodium methylate In dimethyl sulfoxide at 55℃; for 8h;	78%

Cyclopropyl methyl ketone (765-43-5) + 4-nitrobenzaldehdye (555-16-8) → 1-cyclopropyl-3-hydroxy-3-(4-nitrophenyl)propan-1-one (1067243-50-8)

Conditions	Yield
With magnesium iodide diethyletherate; triethylamine In dichloromethane at 20℃; for 0.5h; Catalytic behavior; chemoselective reaction;	99%

Cyclopropyl methyl ketone (765-43-5) → α,α-dichloroethylcyclopropane (40459-85-6)

Conditions	Yield
With phosphorus pentachloride; N-methyl-N-phenylformamide at -25℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere;	98.9%
Stage #1: Cyclopropyl methyl ketone With 1-octyl-3-methyl-imidazolium bromide Stage #2: With thionyl chloride at 30℃; for 4h; Temperature; Reagent/catalyst;	98.9%
With phosphorus pentachloride In 5,5-dimethyl-1,3-cyclohexadiene at -20 - 0℃; for 6h;	84%

Cyclopropyl methyl ketone (765-43-5) + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → 2-cyclopropylpropanal (98485-25-7)

Conditions	Yield
Stage #1: Cyclopropyl methyl ketone; (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran at -10 - 30℃; for 3h; Stage #2: With sulfuric acid In tetrahydrofuran at 60℃; for 1h;	98.2%

Cyclopropyl methyl ketone (765-43-5) → 1-cyclopropylethanol (765-42-4)

Conditions	Yield
With [Re(NH{CH2CH2P(iPr2)}2)(CO)3]Br; potassium tert-butylate; hydrogen In toluene at 110℃; under 22502.3 Torr; for 17h; Inert atmosphere; Glovebox; Autoclave;	98%
With phenylsilane; C14H15MnN5O3(1+)*BF4(1-) In acetonitrile at 80℃; for 5h; Reagent/catalyst;	93%
With lithium aluminium tetrahydride In diethyl ether Reflux;	85%

Cyclopropyl methyl ketone (765-43-5) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyano-3-cyclopropyl-2-butenoate (120109-72-0)

Conditions	Yield
With bis(acetylacetonate)oxovanadium at 20℃; for 4h; Reagent/catalyst; Knoevenagel Condensation;	98%
	50%
With ammonium acetate; acetic acid; benzene

Cyclopropyl methyl ketone (765-43-5) + malononitrile (109-77-3) → 2-(1-cyclopropylethylidene)malononitrile (17407-30-6)

Conditions	Yield
With pyridine; molybdenum hexacarbonyl In 2-methyl-propan-1-ol at 20℃; for 1h;	98%
With ammonium acetate; acetic acid In toluene for 10h; Reflux; Dean-Stark;	80%
	51%

Cyclopropyl methyl ketone (765-43-5) + triphenylphosphine (603-35-0) → (4-Oxo-pentyl)-triphenyl-phosphonium; bromide (112776-51-9)

Conditions	Yield
With hydrogen bromide In chloroform at 120℃; for 24h;	98%

Cyclopropyl methyl ketone (765-43-5) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 1-cyclopropyl-3-(dimethylamino)-2-propen-1-one (21666-68-2)

Conditions	Yield
In N,N-dimethyl-formamide at 110℃; for 24h;	98%
at 20 - 120℃; for 26h;	85%
at 110℃; neat (no solvent);	66%

2-Aminonicotinaldehyde (7521-41-7) + Cyclopropyl methyl ketone (765-43-5) → 2-(cyclopropyl)-1,8-naphthyridine

Conditions	Yield
With sodium hydroxide In ethanol; water for 1h; Friedlaender reaction; Heating;	98%

Cyclopropyl methyl ketone (765-43-5) + 3-nitro-benzaldehyde (99-61-6) → 1-cyclopropyl-3-hydroxy-3-(3-nitrophenyl)-propan-1-one

Conditions	Yield
With magnesium iodide diethyletherate; triethylamine In dichloromethane at 20℃; for 0.5h; Catalytic behavior; chemoselective reaction;	98%

Cyclopropyl methyl ketone (765-43-5) + 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4, 6386-24-9, 6564-72-3, 59531-24-7, 69257-52-9, 78184-89-1, 78609-16-2, 78609-17-3, 78609-18-4, 96553-53-6, 104111-61-7, 131347-08-5, 4132-28-9) → (S,2E,4Z)-4,6-bis(benzyloxy)-1-cyclopropyl-7-hydroxyhepta-2,4-dien-1-one (1569484-09-8)

Conditions	Yield
With tetrabutylammomium bromide; lithium hydroxide In water at 60℃; for 0.25h; Aldol Condensation;	98%

Cyclopropyl methyl ketone (765-43-5) + 2-methanesulfonyl-4-trifluoromethyl-benzonitrile → C14H14F3NO3S

Conditions	Yield
Stage #1: Cyclopropyl methyl ketone With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In toluene Reflux; Large scale; Stage #2: 2-methanesulfonyl-4-trifluoromethyl-benzonitrile In toluene at 60℃; for 5h; Reagent/catalyst; Concentration; Reflux; Large scale;	97.1%

Cyclopropyl methyl ketone (765-43-5) + 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone (154598-53-5) → 2-cyclopropyl-4-(trifluoromethyl)-6-chloroquinoline

Conditions	Yield
With L-proline potassium salt In dimethyl sulfoxide at 20℃; for 18h; Friedlaender Quinoline Synthesis; regioselective reaction;	97%
With L-proline In dimethyl sulfoxide at 50℃; for 48h; Friedlaender synthesis; regioselective reaction;	85%

Cyclopropyl methyl ketone (765-43-5) + phenylacetylene (536-74-3) → 2-cyclopropyl-4-phenylbut-3-yn-2-ol (91909-19-2)

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: Cyclopropyl methyl ketone In tetrahydrofuran; hexane at -78 - 20℃; for 0.666667h; Inert atmosphere;	96%
Stage #1: phenylacetylene With potassium hydroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 0.0833333h; Stage #2: Cyclopropyl methyl ketone at 70℃; for 0.166667h; Further stages.;	85%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane Stage #2: Cyclopropyl methyl ketone In tetrahydrofuran at 0℃; for 2h;	63%

Cyclopropyl methyl ketone (765-43-5) + allylmagnesium bromide (1730-25-2) → 2-cyclopropyl-pent-4-en-2-ol (4743-72-0)

Conditions	Yield
In diethyl ether for 1h; Heating;	96%

Upstream product

• 1487-15-6 2-Methyl-4,5-dihydrofuran 
• 5891-21-4 5-chloro-2-pentanone 
• 3884-71-7 bromo-5-pentanone-2 
• 4663-22-3 isopropenylcyclopropane 
• 56172-71-5 1-Acetylcyclopropane-1-carboxylic acid 
• 75-16-1 methylmagnesium bromide 
• 5500-21-0 cyclopropropanecarbonitrile 
• 24154-06-1 1-chloro-1-cyclopropylethene 
• 75-21-8 oxirane 
• 39743-80-1 (Acetylmethylen)tri(n-butyl)phosphoran 
• 1003-17-4 2,2-dimethyltetrahydrofuran 
• 70058-20-7 1-Cyclopropyl-ethylidene-oxonium 
• 18137-88-7 2-methyleneoxolane 
• 98-01-1 furfural 

Downstream Products

• 92495-63-1 1-cyclopropyl-5t-phenyl-penta-2t,4-dien-1-one 
• 91909-19-2 2-cyclopropyl-4-phenylbut-3-yn-2-ol 
• 1569-44-4 Methylethylallylcarbinol 
• 855918-72-8 4-iodo-4-methyl-hex-1-ene 
• 4435-58-9 2-cyclopropyl-butan-2-ol 
• 37614-38-3 meso-2,3-dicyclopropyl-2,3-butanediol 
• 119778-64-2 2-Cyclopropyl-4-carboxyquinoline 
• 21573-10-4 1-cyclopropyl-butane-1,3-dione 
• 63261-41-6 (E)-1-cyclopropyl-3-phenylpropen-1-one 
• 136120-65-5 1-cyclopropyl-3-phenyl-1-propanone 
• 938-14-7 3-cyclopropyl-3-hydroxy-butyric acid ethyl ester 
• 90482-23-8 1-cyclopropyl-pentane-1,3-dione 
• 168687-97-6 1-cyclopropyl-4-phenyl-butane-1,3-dione 
• 5465-10-1 1-cyclopropyl-3-dimethylamino-1-propanone 

Relevant articles and documents

(Di)triazolylidene manganese complexes in catalytic oxidation of alcohols to ketones and aldehydes

Carbonyl manganese complexes with chelating or bridging mesoionic di(1,2,3-triazolylidene) ligands were efficiently synthesised and fully characterised, including the X-ray diffraction study of a bimetallic manganese(0) complex. This unprecedented bimetallic complex displayed high yield and selectivity in the catalytic oxidation of secondary alcohols and benzyl alcohol with tert-butyl hydroperoxide under mild conditions.

IBX-TfOH mediated oxidation of alcohols to aldehydes and ketones under mild reaction conditions

An efficient, practical and facile procedure has been developed for the oxidation of primary and secondary alcohols using IBX-TfOH catalytic system in 1,4-dioxane at ambient temperature. The reaction affords quantitative yields of the corresponding carbonyl compounds without the formation of over oxidized products. The present synthetic protocol is compatible with a variety of substrates having arene, heteroarene and alkene functionalities. The developed synthetic protocol can be used for higher scale reactions as evident by the oxidation of alcohol at 1 g scale in higher yields by a simple filtration process.

Method for synthesizing cyclopropyl methyl ketone

The synthesis method, uses :1) methylfuran as the raw material 2 - to obtain,chloro - 2 2-pentanone, and the method comprises the following steps ;2): carrying out hydrogen hydrolysis 1) through one-pot hydrogenation hydrolysis, in the presence of the hydrogenation catalyst 5 - hydrogen and water.3). The method 2) for synthesizing the cyclopropylmethyl ketone according to step 5 - comprises the following steps: preparing the cyclopropylmethyl ketone, through a one-pot hydrogenation hydrolysis reaction and a ring-closing reaction step. to prepare the cyclopropylmethyl ketone, by a one-pot, hydrogenation hydrolysis reaction. 2 - The method comprises the following steps: synthesizing,methyl furan as, a raw material, through a one- pot 2 - hydrogenation hydrolysis reaction and, a ring- closing reaction to, prepare the. cyclopropylmethyl ketone by a one- pot hydrogenation hydrolysis reaction and a ring-closing reaction to obtain the cyclopropylmethyl ketone.

Preparation method of 1-chloro-1-chloroacetyl cyclopropane

The invention provides a preparation method of 1-chloro-1-chloroacetyl cyclopropane. The preparation method comprises the following steps: 1)reacting 1, 3-butadiene with diazomethane to generate vinylcyclopropane; 2)reacting the vinyl cyclopropane with an oxidation reagent to generate acetyl cyclopropane; and 3)reacting the acetyl cyclopropane with a chlorination reagent to generate the target product 1-chloro-1-chloroacetyl cyclopropane. The method can reduce the use of strong acids, strong bases and chlorination reagents in the preparation of the 1-chloro-1-chloroacetyl cyclopropane, thereby reducing the discharge of three wastes and lowering the safety risk, and can enhance the synthesis yield to adapt to industrial production.

Safe and environment-friendly preparation method of cyclopropyl acetylene

The invention relates to the field of medicine synthesis, and discloses a safe and environment-friendly preparation method of cyclopropylacetylene, which comprises the following steps: 1) performing chlorination reaction; 2) carrying out an ethynylation reaction; and 3) synthesizing cyclopropyl methyl ketone from the by-product E/Z-2, 5-dichloro-2-pentene. The process provided by the invention ishigh in chlorination yield; the chlorination reagent is triphosgene, the reaction condition is mild, and the safety is high. An organic solvent, inorganic base and a phase transfer catalyst system areadopted in the ethynylation reaction, and the yield is high; the high-flash-point organic solvent dilutes the reaction system, and the reaction is safe. E/Z-2-5-dichloro-2-pentene generated through the chlorination reaction is subjected to sulfuric acid dechlorination and cyclization and then converted into cyclopropyl methyl ketone, and application is achieved. Potassium chloride is treated as aby-product, and an organic solvent, water, organic alkali and a catalyst are used in chlorination reaction; an organic solvent and a phase transfer catalyst used in the ethynylation reaction can be recycled. The reaction is environment-friendly, only two potassium salt byproducts of potassium chloride and potassium sulfate are formed, and zero emission is basically realized.

Chemoselective Oxidation of Equatorial Alcohols with N-Ligated λ3-Iodanes

The site-selective and chemoselective functionalization of alcohols in complex polyols remains a formidable synthetic challenge. Whereas significant advancements have been made in selective derivatization at the oxygen center, chemoselective oxidation to the corresponding carbonyls is less developed. In cyclic systems, whereas the selective oxidation of axial alcohols is well known, a complementary equatorial selective process has not yet been reported. Herein we report the utility of nitrogen-ligated (bis)cationic λ3-iodanes (N-HVIs) for alcohol oxidation and their unprecedented levels of selectivity for the oxidation of equatorial over axial alcohols. The conditions are mild, and the simple pyridine-ligated reagent (Py-HVI) is readily synthesized from commercial PhI(OAc)2 and can be either isolated or generated in situ. Conformational selectivity is demonstrated in both flexible 1,2-substituted cyclohexanols and rigid polyol scaffolds, providing chemists with a novel tool for chemoselective oxidation.

Transfer-dehydrogenation of secondary alcohols catalyzed by manganese NNN-pincer complexes

Novel catalytic systems based on pentacarbonylmanganese bromide and stable NNN-pincer ligands are presented for the transfer-dehydrogenation of secondary alcohols to give the corresponding ketones in good to excellent isolated yields. Best results are obtained using di-picolylamine derivatives as ligands and acetone as an inexpensive hydrogen acceptor. Besides high activity for benzylic substrates, aliphatic alcohols, as well as steroid derivatives, are readily oxidized in the presence of the optimal phosphorus-free catalyst.

Method for synthesizing cyclopropyl methyl ketone by using Alpha-acetyl-Gamma-butyrolactone high-boiling substance

The invention relates to the technical field of chemical synthesis and especially relates to a method for synthesizing cyclopropyl methyl ketone by using Alpha-acetyl-Gamma-butyrolactone high-boilingsubstance. The method for synthesizing cyclopropyl methyl ketone by using Alpha-acetyl-Gamma-butyrolactone high-boiling substance comprises the following steps: (a) uniformly mixing zeolite and concentrated hydrochloric acid, and then adding the high-boiling substance, and reacting for 1-5h while keeping temperature at 80-100 DEG C; standing by and layering after the ending of reaction, and collecting an oil layer; (b) heating an alkaline solution to 70-90 DEG C, adding the oil layer acquired in step (a), and then reacting for 1-5h while keeping temperature at 80-100 DEG C; standing by and layering after the ending of reaction, and collecting the oil layer, thereby acquiring cyclopropyl methyl ketone. According to the invention, three-dimensional well-aligned porous material zeolite and concentrated hydrochloric acid are uniformly mixed with each other, so that the contact area of Alpha-acetyl-Gamma-butyrolactone in high-boiling substance and hydrochloric acid is increased, yield of 5-chlorine-2-pentanone and cyclopropyl methyl ketone is increased and production of by-products is reduced.

Preparation method of 2-chloro-1-(1-chlorocyclopropyl) acetone

The invention relates to the technical field of chemical synthesis, and particularly discloses a preparation method of 2-chloro-1-(1-chlorocyclopropyl) acetone. The preparation method comprises the following steps: enabling alpha-acetyl-gamma butyrolactone and hydrochloric acid to have an open-loop decarboxylic reaction to obtain 5-chloro-2-pentanone; adding the 5-chloro-2-pentanone and a catalystinto an alkaline solution, implementing a cyclization reaction, obtaining cyclopropyl methyl ketone; implementing a chlorination reaction with a chloride agent to obtain the 2-chloro-1-(1-chlorocyclopropyl) acetone. The reaction steps of the provided method are less, the reaction period is short, the yield is more than 70%, and the content of the 2-chloro-1-(1-chlorocyclopropyl) acetone in a product is more than 95%.