504-02-9

Basic information

• Product Name: 1,3-Cyclohexanedione
• Synonyms: 1,3-Cyclohexanedione, 97% 500GR;Dihydro-1,3-benzenediol;NSC 57477;1,3-Cyclohexanedione 97%;1,3-Cyclohexanedione SynonyMs Cyclohexane-1,3-dione;1,3-Benzenediol, dihydro-;1,3-Cyclohexandione;Hydroresorcinol
• CAS NO: 504-02-9
• Molecular Formula: C6H8O2
• Molecular Weight: 112.13
• EINECS: 207-980-0
• Product Categories: cyclic compounds;ketone;Analytical Chemistry;Carbonyl Group Labeling Reagents for Fluorescence HPLC;Fluorescence Detection (HPLC Labeling Reagents);HPLC Labeling Reagents;Intermediates;Isotope Labelled Compounds
• Mol File: 504-02-9.mol

Chemical Properties

• Melting Point: 101-105 °C(lit.)
• Boiling Point: 170.05°C (rough estimate)
• Flash Point: 85.7 °C
• Appearance: Pale yellow to beige/Powder
• Density: 1,1 g/cm3
• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: 1.4576 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 5.26(at 25℃)
• Water Solubility: soluble
• Merck: 14,3178
• BRN: 385888
• CAS DataBase Reference: 1,3-Cyclohexanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexanedione(504-02-9)
• EPA Substance Registry System: 1,3-Cyclohexanedione(504-02-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: GV0350000
• F: 8-21
• TSCA: Yes
• Hazardous Substances Data: 504-02-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,3-Cyclohexanedione is used as a building block for the synthesis of various organic compounds. It serves as an intermediate in the production of herbicides such as sulcotrione and nitrosulfonone, as well as in the synthesis of the pharmaceutical intermediate nitisinone.
Used in Pharmaceutical Intermediates:
1,3-Cyclohexanedione is used as a pharmaceutical intermediate, playing a crucial role in the development of new drugs and therapeutic agents.
Used in the Synthesis of 9-substituted 1,8-dioxo-xanthenes:
1,3-Cyclohexanedione is used as a reactant in the synthesis of 9-substituted 1,8-dioxo-xanthenes by reacting with unactivated aldehydes through an aldol condensation/Michael addition reaction.
Used in the Synthesis of [(1,2,3-triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives:
1,3-Cyclohexanedione is used as a reactant in the synthesis of [(1,2,3-triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives by treating with phthalhydrazide, aromatic propargyloxy aldehydes, and azides via a four-component condensation reaction.
Used in the Preparation of 2-substituted Adducts:
1,3-Cyclohexanedione is used to prepare 2-substituted adducts, which are important intermediates for the synthesis of various compounds, including ?-enaminones, polyhydroquinoline derivatives, 1,8-dioxo-dodecahydroxanthenes, spirocyclopentanols, oxathioles, and triquinanes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 3206, 1965 DOI: 10.1021/jo01020a506

Purification Methods

Crystallise the dione from *benzene. Dissolve ~50g of the diol in 140mL of *C6H6 under N2, cool, collect the solid and dry it in a vacuum desiccator overnight. It is unstable and should be stored under N2 or Ar at ~0o. [Thompson Org Synth Coll Vol III 278 1955, Beilstein 7 IV 1985.]

InChI:InChI=1/C6H8O2/c7-5-2-1-3-6(8)4-5/h4,7H,1-3H2

Synthetic route

3-Ethoxycyclohex-2-en-1-one (5323-87-5) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With water at 20℃; under 900.09 Torr; for 0.226667h; Flow reactor;	99%
With ammonium cerium(IV) nitrate In water; acetonitrile for 0.5h; Heating;	92%
With iron(III) chloride hexahydrate In water at 25℃; for 12h;

3-butanoxycyclohex-2-en-1-one (16493-04-2) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With water In acetonitrile at 20℃; under 900.09 Torr; for 0.226667h; Flow reactor;	99%
With ammonium cerium(IV) nitrate In water; acetonitrile for 0.75h; Heating;	90%
Multi-step reaction with 2 steps 1: Amberlyst-15 / 80 °C / 2475.25 Torr 2: water / Flow reactor View Scheme

3-(propoxy)cyclohex-2-en-1-one (104808-17-5) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With water In acetonitrile at 20℃; under 900.09 Torr; for 0.226667h; Flow reactor;	99%
Multi-step reaction with 2 steps 1: Amberlyst-15 / 80 °C / 2475.25 Torr 2: water / acetonitrile / 0.23 h / 20 °C / 900.09 Torr / Flow reactor View Scheme
Multi-step reaction with 3 steps 1: Amberlyst-15 / 80 °C / 2475.25 Torr 2: Amberlyst-15 / 80 °C / 2475.25 Torr 3: water / Flow reactor View Scheme

3-methoxycyclohex-2-en-1-one (16807-60-6) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With water at 20℃; under 900.09 Torr; for 0.226667h; Flow reactor;	98%
With ammonium cerium(IV) nitrate In water; acetonitrile for 0.5h; Heating;	91%
Multi-step reaction with 2 steps 1: Amberlyst-15 / 80 °C / 2475.25 Torr 2: water / 0.23 h / 20 °C / 900.09 Torr / Flow reactor View Scheme

cyclohexane-1,3-dione sodium enolate (1874-83-5) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With hydrogenchloride In water at 15 - 20℃;	96.43%

recorcinol (108-46-3) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With hydrogen In dichloromethane at 30℃; under 7500.75 Torr; for 6h; Reagent/catalyst; Temperature; Pressure; Autoclave;	94%
Stage #1: recorcinol With sodium hydroxide In water at 15℃; Stage #2: With platinum on activated charcoal; hydrogen In water at 80 - 105℃; under 7500.75 Torr; for 5h; Stage #3: With hydrogenchloride In water at 18℃; Temperature; Pressure;	93%
With sodium hydroxide In aluminum nickel; water; hydrogen	91%

1,4-dioxaspiro[4.5]decan-7-one (4969-01-1) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With sulfuric acid; silica gel In dichloromethane for 6h; Ambient temperature;	93%
With pyridinium p-toluenesulfonate; silica gel In water for 0.05h; microwave irradiation;	81%
With sulfuric acid In dichloromethane for 20h; Ambient temperature;	70%
With sulfuric acid; silica gel In dichloromethane for 24h; Ambient temperature;	60%

C12H16O6 → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With water; sodium hydroxide at 70 - 80℃; for 2h; Temperature;	90.5%

C10H12O6 → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With water; sodium hydroxide at 60 - 70℃; for 2h; Temperature;	90.2%

1,4,8,11-tetraoxa-dispiro[4.1.4.3]tetradecane (177-77-5) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With pyridinium p-toluenesulfonate; silica gel In water for 0.05h; microwave irradiation;	89%

3-benzyloxy-2-cyclohexenone (69016-26-8) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile for 0.75h; Heating;	88%

3-(hexyloxy)cyclohex-2-en-1-one → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile for 1h; Heating;	84%
With iron(III) chloride hexahydrate In water at 25℃; for 12h;
With water Flow reactor;

3-phenethyloxy-cyclohex-2-enone → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile for 1h; Heating;	83%

1,5-dithiaspiro<5.5>undecan-8-one (128345-12-0) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With acetic acid at 35℃; for 8h;	81%

methyl levulinate (13984-50-4) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With sodium methylate In methanol Heating;	80%
Stage #1: methyl levulinate With potassium tert-butylate In tetrahydrofuran for 6h; Reflux; Stage #2: With hydrogenchloride In water	74%

3-isopropoxycyclohex-2-en-1-one (58529-72-9) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile for 2.5h; Heating;	80%

1-Trimethylsiloxy-bicyclo[3.1.0]hexan (50338-46-0) → 3-hydroxycyclohexanone (823-19-8) + 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With bis(acetylacetonate)oxovanadium; oxygen In ethanol Ambient temperature;	A 75% B 10%
With vanadyl acetylacetonate; oxygen In ethanol at 20℃; for 20h;	A 75% B 10%

2-(1,3-Diphenyl-3-oxopropyl)cyclohexane-1,3-dione (53852-96-3) → (+/-)-trans-2-benzoyl-3-phenyl-2,3,6,7-tetrahydrobenzo-furan-4(5H)-one + 1,3-cylohexanedione (504-02-9) + benzalacetophenone (94-41-7)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; potassium tert-butylate; tetra-(n-butyl)ammonium iodide In acetonitrile at 30℃; for 12h;	A 15% B 69% C 74%

formaldehyd (50-00-0) + 1,3-cyclopentadione (3859-41-4) → 1,3-cylohexanedione (504-02-9) + 6,7-dihydrocyclopenta[d][1,3]dioxin-5(4H)-one (102306-78-5)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane for 38h; Product distribution; Ambient temperature; var. 1,3-cyclodienones; var. forms of CH2O, var. time;	A 9% B 73%

Cyclohexane-1,3-dione Dioxime → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With hexamethylenetetramine; water for 0.005h; microwave irradiation;	72%

6-(3-Benzyloxy-propyl)-7-oxa-bicyclo[4.1.0]heptan-2-one (144730-04-1) → 1,3-cylohexanedione (504-02-9) + 3-[3-(benzyloxy)propyl]cyclohex-2-enone (144730-20-1) + (3aS,7aS)-3-Benzyloxy-7a-hydroxy-octahydro-inden-4-one (144730-08-5, 144730-09-6)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;	A 5% B 4% C 67%

7-oxabicyclo[4.1.0]heptan-2-one (6705-49-3) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In water; toluene at 80℃; for 24h;	62%
With 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene bis(2,2-dimethylpropanoate); tetrakis(triphenylphosphine) palladium(0) In water; toluene at 80℃; for 24h;	62.3%

2-Hydroxy-2-methoxymethyl-cyclopentanone (78743-56-3) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With potassium hydrogensulfate at 170 - 180℃; under 20 - 25 Torr;	61%

6-(3-Phenyl-propyl)-7-oxa-bicyclo[4.1.0]heptan-2-one (144730-03-0) → 1,3-cylohexanedione (504-02-9) + 3-(3-Phenyl-propyl)-cyclohex-2-enone (144730-06-3) + (3R,3aR,7aR)-7a-Hydroxy-3-phenyl-octahydro-inden-4-one (144730-05-2, 144730-21-2)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;	A 8% B 8% C 61%

acetone (67-64-1) + ethyl acrylate (140-88-5) → ethyl 3-ethoxypropionate (763-69-9) + ethyl 3-(2,4-dioxocyclohexyl)propanoate (1335209-87-4) + 1,3-cylohexanedione (504-02-9)

Conditions	Yield
With sodium hydride In toluene at -10 - 20℃; for 2h; Michael-Claisen cyclization; Inert atmosphere; regioselective reaction;	A 8% B 54% C 3%
With sodium hydride at -10 - 20℃; for 0.0833333h; Michael-Claisen cyclization; Inert atmosphere; neat (no solvent); regioselective reaction;	A 6% B 39% C 9%

6-(4-Pentenyl)-7-oxabicyclo<4.1.0>heptan-2-one (135525-28-9) → 3-(4-pentenyl)-2-cyclohexen-1-one (70079-75-3) + 1,3-cylohexanedione (504-02-9) + (3aS,7aS)-7a-Hydroxy-3-vinyl-octahydro-inden-4-one (144730-18-7, 144730-19-8)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;	A 13% B 7% C 51%

2-Diazo-3-hydroxy-1-cyclohexanone (81902-29-6) → cyclopent-1-enecarboxylic acid (1560-11-8) + 2-formylcyclopentanone (1192-54-7) + C12H14O3 (54170-83-1) + (+/-)-(1R,2R)-trans-2-hydroxy-1-cyclopentanecarboxylic acid (1883-88-1, 17502-28-2, 63578-05-2, 63578-06-3, 81887-89-0, 125072-73-3) + 1,3-cylohexanedione (504-02-9) + 2-Hydroxy-cyclopentanecarboxylic acid 2-oxo-cyclopent-(Z)-ylidenemethyl ester (81887-95-8)

Conditions	Yield
In tetrahydrofuran; water at 20 - 25℃; for 2h; Product distribution; Mechanism; Irradiation; different reaction time;	A 49% B 1% C n/a D 27% E n/a F 8%

3,5-dihydroxyphenol (108-73-6) → 1,3-cylohexanedione (504-02-9) + recorcinol (108-46-3)

Conditions	Yield
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 6h;	A 48.9% B 28.8%

(BiClPh3)2 O + 3-hydroxycyclohexanone (823-19-8) + potassium carbonate (584-08-7) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
In dichloromethane	9.4%

ethanol (64-17-5) + ethyl 2-carbethoxy-5-oxocaproate (4761-26-6) + sodium ethanolate (141-52-6) → 1,3-cylohexanedione (504-02-9)

Conditions	Yield
2 Tage;

1,3-cylohexanedione (504-02-9) → 2-bromocyclohexane-1,3-dienone (60060-44-8)

Conditions	Yield
With bromine; acetic acid at 20℃;	100%
With bromine In acetic acid at 20℃; for 2h;	100%
With bromine; acetic acid at 20℃; for 3h; Cooling with ice;	98%

ethanol (64-17-5) + 1,3-cylohexanedione (504-02-9) → 3-Ethoxycyclohex-2-en-1-one (5323-87-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Reflux;	100%
With hydrogenchloride at 20℃; for 24h;	100%
With Amberlyst-15 at 80℃; under 2475.25 Torr; for 0.0766667h; Catalytic behavior; Temperature; Concentration; Flow reactor;	99%

1,3-cylohexanedione (504-02-9) + 4-chloro-aniline (106-47-8) → 3-(4-choloroaniline)-2-cyclohexen-1-one (36646-75-0)

Conditions	Yield
at 20℃; for 0.5h; Solid phase reaction; condensation;	100%
With silica In neat (no solvent) at 20℃; for 0.666667h; Green chemistry;	98%
With ytterbium(III) triflate In acetonitrile at 20℃; for 0.5h;	91%

Ketene (463-51-4) + 1,3-cylohexanedione (504-02-9) → 3-acetoxy-cyclohex-2-enone (57918-73-7)

Conditions	Yield
With acetic anhydride for 0.133333h; Ambient temperature;	100%

ethyl Bromopyruvate (70-23-5) + 1,3-cylohexanedione (504-02-9) → 3-hydroxy-4-oxo-2,3,4,5,6,7-hexahydrobenzofuran-3-carboxylic acid ethyl ester (128428-59-1)

Conditions	Yield
With potassium hydroxide In methanol Ambient temperature; overnight;	100%
With 1-butyl-3-methylimidazolium hydroxide at 25 - 30℃; for 0.5h; Feist-Benary reaction;	88%
Stage #1: 1,3-cylohexanedione With ammonium acetate In ethanol; water at 80℃; for 1h; Stage #2: ethyl Bromopyruvate In ethanol; water at 80℃; for 3h;	88%
With sodium hydroxide In methanol for 12h; microwave heating;

1,3-cylohexanedione (504-02-9) + 4-methoxy-aniline (104-94-9) → 3-(4-methoxyphenylamino)cyclohex-2-en-1-one (36646-77-2)

Conditions	Yield
at 20℃; for 0.5h; Solid phase reaction; condensation;	100%
With ytterbium(III) triflate In acetonitrile at 20℃; for 0.333333h;	97%
With ytterbium(III) triflate In acetonitrile at 20℃; Inert atmosphere;	97%

1,3-cylohexanedione (504-02-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-(dimethylaminomethylene)cyclohexane-1,3-dione (85302-07-4)

Conditions	Yield
for 1h; Heating;	100%
at 100℃; for 1h;	100%
at 95℃; for 1h;	100%

1,3-cylohexanedione (504-02-9) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → 2-(dimethylaminomethylene)cyclohexane-1,3-dione (85302-07-4)

Conditions	Yield
In benzene for 0.333333h; Heating;	100%

nonadecanoyl chloride (59410-47-8) + 1,3-cylohexanedione (504-02-9) → Nonadecanoic acid 3-oxo-cyclohex-1-enyl ester

Conditions	Yield
With pyridine In chloroform for 1h;	100%

1,3-cylohexanedione (504-02-9) + ethylene glycol (107-21-1) → 1,4,8,11-tetraoxa-dispiro[4.1.4.3]tetradecane (177-77-5)

Conditions	Yield
With zeolite HSZ-360 In toluene for 8h; Heating;	100%

1,3-cylohexanedione (504-02-9) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → 9-phenyl-3,4-dihydro-2H-acridin-1-one (17401-27-3)

Conditions	Yield
With o-benzenedisulfonimide at 80℃; for 4h; Friedlaender synthesis; Neat (no solvent);	100%
With 3-methyl-1-sulfoimidazolium trichloroacetate; trichloroacetic acid In neat (no solvent) at 100℃; Friedlaender Quinoline Synthesis;	100%
With aluminum oxide In chloroform for 3h; Friedlaender reaction; Reflux;	98%

1,3-cylohexanedione (504-02-9) + p-toluidine (106-49-0) → 3-(p-tolylamino)cyclohex-2-en-1-one (36646-74-9)

Conditions	Yield
at 20℃; for 0.5h; Solid phase reaction; condensation;	100%
With ytterbium(III) triflate In acetonitrile at 20℃; for 0.333333h;	96%
With acetic acid In toluene at 110℃; for 4h;	96%

5-((E)-2-nitroethenyl)-1,3-benzodioxole (1485-00-3, 22568-48-5) + 1,3-cylohexanedione (504-02-9) → 2-(1-benzo[1,3]dioxol-5-yl-2-nitro-ethyl)-3-hydroxy-cyclohex-2-enone (363593-22-0)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 18℃; for 2h; Michael addition;	100%

4-methyl-benzaldehyde (104-87-0) + ethyl acetoacetate (141-97-9) + 1,3-cylohexanedione (504-02-9) → ethyl 2-methyl-4-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Conditions	Yield
With Cu(OTf)2; ammonium acetate In ethanol at 100℃; for 0.25h; Hantzsch reaction; Microwave irradiation;	100%
With ammonium acetate; ethanol; iodine at 40℃; for 0.583333h; Hantzsch reaction;	99%
With ammonium acetate; ammonium cerium(IV) nitrate In ethanol at 20℃; for 1.5h; Hantzsch dihydropyridine synthesis;	98%

1,3-cylohexanedione (504-02-9) + Propargylamine (2450-71-7) → (N-propargyl)-3-amino-2-cyclohexenone (69042-21-3)

Conditions	Yield
In benzene for 12h; Heating;	100%
In benzene Reflux;	91%
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 0.5h;	79%
In neat (no solvent) at 20℃; for 14h; Green chemistry;
In neat (no solvent) at 20℃; for 24h;

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + 1,3-cylohexanedione (504-02-9) → 3-(tert-butoxy)cyclohex-2-en-1-one (95849-54-0)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane; cyclohexane for 2h;	100%

1,3-cylohexanedione (504-02-9) + 2-aminoacetophenone (551-93-9) → 9-methyl-3,4-dihydro-2H-acridin-1-one (14428-46-7)

Conditions	Yield
With o-benzenedisulfonimide at 80℃; for 16h; Friedlaender synthesis; Neat (no solvent);	100%
With toluene-4-sulfonic acid for 0.0833333h; Friedlaender condensation; Heating;	96%
With γ-Fe2O3-HAp-Si-(CH2)3-NHSO3H nanoparticles at 20℃; for 1.5h; Friedlaender synthesis; neat (no solvent);	96%

5-amino-2-methoxyphenol (1687-53-2) + 1,3-cylohexanedione (504-02-9) → 3-(3-hydroxy-4-methoxyanilino)-2-cyclohexen-1-one

Conditions	Yield
With toluene-4-sulfonic acid In benzene	100%

1,3-cylohexanedione (504-02-9) + L-proline (147-85-3) → 1-(3-oxocyclohex-1-enyl)pyrrolidine-2-carboxylic acid (1033193-52-0)

Conditions	Yield
In benzene for 5h; Reflux;	100%

ethyl acetoacetate (141-97-9) + 1,3-cylohexanedione (504-02-9) + 4-(Methylthio)benzaldehyde (3446-89-7) → 2-Methyl-4-(4-methylsulfanyl-phenyl)-5-oxo-1,4, 5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester (312527-79-0)

Conditions	Yield
With Cu(OTf)2; ammonium acetate In ethanol at 100℃; for 0.25h; Hantzsch reaction; Microwave irradiation;	100%

indan-1,2,3-trione hydrate (485-47-2) + 1,3-cylohexanedione (504-02-9) → 4b,9b-dihydroxy-7,8-dihydro-4bH-indeno[1,2-b]benzofuran-9,10(6H,9bH)-dione (374918-82-8)

Conditions	Yield
With acetic acid for 0.25h; Heating;	100%

2-[1-(4-fluorophenyl)ethenyl]thiophene (1343477-51-9) + 1,3-cylohexanedione (504-02-9) → 2-(4-fluorophenyl)-3,5,6,7-tetrahydro-2-(2-thienyl)benzofuran-4(2H)-one (1378021-29-4)

Conditions	Yield
With manganese(III) triacetate dihydrate; acetic acid at 50 - 80℃; Inert atmosphere;	100%

ethyl α-nitrocinnamate (18315-80-5, 18315-86-1, 16508-09-1) + 1,3-cylohexanedione (504-02-9) → ethyl 4-oxo-3-phenyl-2,3,4,5,6,7-hexahydrobenzofuran-2-carboxylate (1399075-98-9)

Conditions	Yield
With triethylamine In acetonitrile at 60℃; for 3h;	100%
With tetrabutylammomium bromide; triethylamine In water at 70℃; for 6h;	85%

1,3-cylohexanedione (504-02-9) + diethyl 5-formyl-3-methyl-1-(2-oxo-2-phenylethyl)-1H-pyrrole-2,4-dicarboxylate → diethyl 5-benzoyl-2-methyl-9-oxo-6,7,8,9-tetrahydropyrrolo[1,2-b]isoquinoline-1,3-dicarboxylate

Conditions	Yield
With piperdinium acetate In ethanol at 120℃; for 24h;	100%

R,S-trans-2-aminocyclohexan-1-ol + 1,3-cylohexanedione (504-02-9) → trans-3-(2-hydroxycyclohexyl)amino-2-cyclohexenone

Conditions	Yield
In toluene at 135℃; for 1h;	99.7%

2-chloro-benzaldehyde (89-98-5) + 1,3-cylohexanedione (504-02-9) → C19H19ClO4 (152129-14-1)

Conditions	Yield
With piperidine In ethanol; water at 20℃; for 0.333333h;	99.65%
In methanol; water at 40 - 45℃; for 0.166667h;	96%
With cesium fluoride In ethanol at 20℃; for 0.333333h;	91%
With potassium hydroxide In ethanol for 2h; Condensation; Heating;

1,3-cylohexanedione (504-02-9) + 3-Chlorobenzaldehyde (587-04-2) → 2,2'-(3''-chlorophenyl)methylene-bis(cyclohexane-1,3-dione)

Conditions	Yield
With piperidine In ethanol; water at 20℃; for 0.333333h;	99.65%
With silica gel; aniline; ytterbium(III) triflate at 20℃; for 0.0333333h; neat (no solvent, solid phase);	87%

1,3-cylohexanedione (504-02-9) + ortho-bromobenzaldehyde (6630-33-7) → 2,2'-((2-bromophenyl)methylene)dicyclohexane-1,3-dione

Conditions	Yield
With piperidine In ethanol; water at 20℃; for 0.333333h;	99.65%
In water at 20℃; for 4h;	85%

1,3-cylohexanedione (504-02-9) + m-aminobenzaldehyde (1709-44-0) → C19H21NO4

Conditions	Yield
With piperidine In ethanol; water at 20℃; for 0.333333h;	99.65%

1,2,3-Benzotriazole (95-14-7) + 6-bromo-2-hydroxy-3-methoxybenzaldehyde (20035-41-0) + 1,3-cylohexanedione (504-02-9) → 9-benzotriazol-1-yl-8-bromo-5-methoxy-2,3,4,9-tetrahydroxanthen-1-one

Conditions	Yield
With hydroxy proline Reagent/catalyst; Green chemistry;	99.5%

Upstream product

• 64-17-5 ethanol 
• 4761-26-6 ethyl 2-carbethoxy-5-oxocaproate 
• 141-52-6 sodium ethanolate 
• 53293-00-8 hex-5-ynoic acid 
• 13984-57-1 ethyl 5-oxohexanoate 
• 533-73-3 1,2,4-Trihydroxybenzene 
• 2802-07-5 1,3-cyclohexanedionedioxime 
• 108-94-1 cyclohexanone 
• 407-25-0 trifluoroacetic anhydride 
• 108-46-3 recorcinol 
• 3740-59-8 3,4-dihydro-6-methyl-2H-pyran-2-one 
• 6705-49-3 7-oxabicyclo[4.1.0]heptan-2-one 
• 50-00-0 formaldehyd 
• 3859-41-4 1,3-cyclopentadione 

Downstream Products

• 19805-73-3 3-(pyrrolidin-1-yl)cyclohex-2-en-1-one 
• 16807-60-6 3-methoxycyclohex-2-en-1-one 
• 53852-96-3 2-(1,3-Diphenyl-3-oxopropyl)cyclohexane-1,3-dione 
• 143673-42-1 2,2 '-(furan-2-ylmethylene)dicyclohexane-1, 3-dione 
• 54135-60-3 2,2'-methylenebis(cyclohexane-1,3-dione) 
• 51532-41-3 bis(succinimidomethyl) ether 
• 69375-51-5 N-(2,6-dioxo-cyclohexylmethyl)-phthalimide 
• 6868-85-5 3',4',6',7'-tetrahydro-spiro<3H-indole-3-9'-<9H>xantene>-1',2,8'(1H,2'H,5'H)-trione 
• 95200-84-3 9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 
• 57918-73-7 3-acetoxy-cyclohex-2-enone 
• 4056-73-9 2-acetyl-1,3-cyclohexanedione 
• 107775-56-4 4-(2-chlorophenyl)-3,4,7,8-tetrahydro-1H,6H-quinazolin-2,5-dione 
• 23062-84-2 4-phenyl-4,6,7,8-tetrahydro-benzo[e][1,2]oxazine-3,5-dione 
• 56946-66-8 2-(3-methylbut-2-en-1-yl)cyclohexane-1,3-dione 

Relevant articles and documents

Method for preparing 1, 3-cyclohexanedione

The invention discloses a method for preparing 1, 3-cyclohexanedione. The method comprises the following steps: 1) dissolving acetylacetone and a catalyst in a solvent, adding acrylate into a constant-pressure dropping funnel, and dropwise adding acrylate into a reaction system, after drop-by-drop adding, heating to 60-80 DEG C, and continuously reacting for 0.5-1 hour; and 2) after the reaction is finished, cooling to 40 DEG C, adding a solid condensing agent, heating the reaction liquid to 40-50 DEG C, continuously reacting for 1-1.5 hours, concentrating under reduced pressure to remove the solvent and methyl acetate and other low-boiling-point byproducts generated by the reaction, then adding a small amount of water, adjusting the pH value to 1-2 by using hydrochloric acid (1.1-1.2 equivalent), cooling to separate out a product, centrifuging, leaching by using a small amount of ice water, carrying out pulping treatment by using ethyl acetate, filtering and drying to obtain the 1, 3-cyclohexanedione product.

Method for synthesizing 1,3-cyclohexanedione by utilizing platinum-carbon catalytic reaction

The invention discloses a method for synthesizing 1,3-cyclohexanedione by utilizing a platinum-carbon catalytic reaction, and belongs to the technical field of chemical industry. The method comprisesthe following steps: mixing and dissolving resorcinol and sodium hydroxide into deionized water, carrying out a reaction at a temperature of 5-15 DEG C to prepare a resorcinol solution, carrying out heat preservation and pressure maintaining treatment for 45-90 minutes, adding a platinum-carbon catalyst, stirring, carrying out a reaction for 15 to 20 hours, obtaining a black solid after the metalions in the solution are completely reduced, and washing sequentially with distilled water and ethanol to obtain a 1,3-cyclohexanedione crude product. According to the invention, the platinum-carbon catalyst adopted as a reduction reaction catalyst has great economic advantages and great safety advantages compared with the traditional Raney nickel catalyst, the risk easily occurring during the production process is avoided, and the yield and the quality of the product are improved.

Preparation method of 1,3-cyclohexanedione

The invention relates to the field of organic synthesis, and discloses a preparation method of 1,3-cyclohexanedione. The method comprises the following steps: 1, in the presence of water, hydrogenating resorcinol to obtain a reaction solution containing a compound represented by the following formula (1), acidifying the reaction solution to obtain an acidified solution, and crystallizing the acidified solution to obtain a 1,3-cyclohexanedione product and an acidified mother liquor; 2, in the presence of an organic solvent, enabling the acidified mother liquor to be in contact with a complexingagent to complex 1,3-cyclohexanedione with the complexing agent, and obtaining an organic phase; 3, making the organic phase obtained in the step 2 contact the reaction solution, adjusting the pH value to 7-14 so as to make the 1,3-cyclohexanedione be dissociated from the complexing agent, and obtaining a water phase; and 4, adjusting the pH value of the water phase obtained in the step 3 to 1.0-2.5, and carrying out solid-liquid separation to obtain the 1,3-cyclohexanedione product. The preparation method disclosed by the invention has the advantages of high purity and high yield of the prepared 1,3-cyclohexanedione.

Preparation method of 1,3-cyclohexanedione

The invention relates to the technical field of chemical synthesis, in particular to a preparation method of 1,3-cyclohexanedione. The preparation method of the 1,3-cyclohexanedione comprises the following steps: with 1,3-acetonedicarboxylic ester and acrylate as raw materials, carrying out condensation and cyclization under the action of a base catalyst to prepare an intermediate; carrying out hydrolysis decarboxylation on the intermediate to obtain a crude product; and recrystallizing the crude product to obtain the 1,3-cyclohexanedione. The preparation method of the 1,3-cyclohexanedione hasthe advantages that process conditions are convenient to realize, post-treatment operation process is simple, yield is as high as 90.9%, reaction selectivity is high, production efficiency is high, operation safety is high, pollution is small, and the preparation method is suitable for industrial scale production.

Reversible chemoselective transetherification of vinylogous esters using Fe-catalyst under additive free conditions

An additive/Br?nsted acid/base free, highly efficient and chemoselective transetherification of electron deficient vinylogous esters and water mediated de-alkylation using an earth-abundant Fe-catalyst under very mild reaction conditions is described. This reaction is highly selective to primary alcohols over secondary alcohols, has good functional group tolerance, is scalable to gram scale and a purification free sequential transetherification in a continuous flow mode is demonstrated.

Rapid and Multigram Synthesis of Vinylogous Esters under Continuous Flow: An Access to Transetherification and Reverse Reaction of Vinylogous Esters

An environmentally benign approach for the synthesis of vinylogous esters from 1,3-diketone and its reverse reaction under continuous-flow has been developed with alcohols in the presence of inexpensive Amberlyst-15 as a catalyst. This methodology is highly selective and general for a range of cyclic 1,3-dicarbonyl compounds which gives a library of linear alkylated and arylated vinylogous esters in good to excellent yield under solvent and metal free condition. Furthermore, the long-time experiment in a continuous-flow up to 40 h afforded 8.0 g of the vinylogous ester with turnover number (TON) = 28.6 and turnover frequency (TOF) = 0.715 h-1 using Amberlyst-15 as a catalyst. Furthermore, a continuous-flow sequential transetherification of vinylogous esters with various alcohols has been achieved in high yield. Reversibly, this vinylogous ester was deprotected or hydrolyzed into ketone using environmentally benign water as a solvent and Amberlyst-15 as a catalyst under continuous-flow process.

Method for preparing 1,3-cyclohexanedione through gas-phase hydrogenation of resorcinol

The invention provides a method for preparing 1,3-cyclohexanedione through gas-phase hydrogenation of resorcinol. The method comprises the following steps: dissolving resorcinol in benzene, then subjecting the dissolved resorcinol to direct vaporization, and mixing the vaporized resorcinol with hydrogen; allowing a mixture obtained in the previous step to pass through a fixed-bed reactor filled with an activated carbon-supported palladium catalyst at a mass space velocity of 0.1/h to 0.7/h, and controlling a molar ratio of hydrogen to phenol to be 2/1 to 10/1, a reaction temperature to be 180-280 DEG C and a reaction pressure of 1.0-2.0 MPa; and condensing a product obtained in the previous step with a condenser so as to obtain the hydrogenation product, i.e., 1,3-cyclohexanedione. As themethod is used for preparation of 1,3-cyclohexanedione, the conversion rate of resorcinol is up to 99.9%, and the selectivity of 1,3-cyclohexanedione is up to 97.8%.

Palladium graphene selective catalytic hydrogenation process for preparing 1, 3 - Cyclohexanedione method (by machine translation)

The invention discloses a palladium graphene selective catalytic hydrogenation process for preparing 1, 3 - Cyclohexanedione method: in the reactor, adding catalyst palladium graphene, raw material resorcinol soluble in the solvent dichloromethane solution, the hydrogen gas, the hydrogen pressure is 0.1 - 2 mpa, temperature is 20 - 60 °C reaction under the condition of 0.5 - 3h after, processing reaction liquid to obtain product 1, 3 - Cyclohexanedione; this invention adopts the palladium graphene selective catalytic hydrogenation resorcinol preparing 1, 3 - Cyclohexanedione method, with the traditional process for preparing 1, 3 - Cyclohexanedione processes of the prior art, avoids the use of large amount of organic and inorganic salt, the operation process is simple and easy, high conversion rate and selectivity, has very high innovative and industrial application value. (by machine translation)

1,3-cyclohexanedione preparation method

The invention discloses a 1,3-cyclohexanedione preparation method, which comprises: (1) salt forming: mixing and dissolving resorcinol and sodium hydroxide in deionized water, and carrying out a reaction at a temperature of 5-15 DEG C; (2) hydrogenation reducing: transferring the salt-forming solution obtained in step (1) into a hydrogenation kettle, adding a platinum-carbon catalyst, introducing hydrogen gas after completing the displacement, stirring, and carrying out a reaction, wherein the reaction pressure is 1.2-1.5 MPa, and the reaction temperature is 95-105 DEG C; and (3) acidification: acidifying the filtrate obtained in step (2) at a temperature of 0-15 DEG C. According to the present invention, the preparation method has advantages of low risk, high application times, high yield, and high product purity.

Transformation of the Herbicide Sulcotrione into a Root Growth Enhancer Compound by Sequential Photolysis and Hydrolysis

Xanthene-1,9-dione-3,4-dihydro-6-methylsulfonyl (1), the main product of sulcotrione phototransformation on plant leaves, was slowly hydrolyzed into 2-hydroxy-4-methylsulfonylbenzoic acid (2) and 1,3-cyclohexanedione (3) in aqueous solution. Interestingly, the rate of hydrolysis was significantly enhanced in the presence of roots of monocotyledonous plants, while the same treatment showed adverse effects on broadleaf weeds. Root growth enhancement varied according to the plant species and concentrations of compound 2, as shown with Zea mays roots. Compound 2 is a derivative of salicylic acid that is known to be a plant signaling messenger. Compound 2 was, therefore, able to mimic some known effects of this phytohormone. This work showed that a pesticide like sulcotrione was transformed into a compound exhibiting a positive impact on plant growth. This study exemplified a rarely reported situation where chemical and biological chain reactions transformed a xenobiotic into a compound exhibiting potential beneficial effects.