490-78-8

Basic information

• Product Name: 2',5'-Dihydroxyacetophenone
• Synonyms: 1-(2,5-dihydroxyphenyl)-ethanon;1-Acetyl-2,5-dihydroxybenzene;2,5-Dihydroxy-1-acetylbenzene;2’,5’-dihydroxy-acetophenon;Acetophenone, 2',5'-dihydroxy-;Acetylhydroquinone;QUINACETOPHENONE;ACETYLQUINOL
• CAS NO: 490-78-8
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 207-716-4
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Acetophenones & Derivatives (substituted);Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 490-78-8.mol
• Article Data: 62

Chemical Properties

• Melting Point: 204-206 °C(lit.)
• Boiling Point: 234.6°C (rough estimate)
• Flash Point: 167.1 °C
• Appearance: Yellow to yellow-green/Crystals or Crystalline Powder
• Density: 1.2143 (rough estimate)
• Refractive Index: 1.4447 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: dioxane: 50 mg/mL, clear
• PKA: 9.86±0.18(Predicted)
• Water Solubility: insoluble
• BRN: 637903
• CAS DataBase Reference: 2',5'-Dihydroxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2',5'-Dihydroxyacetophenone(490-78-8)
• EPA Substance Registry System: 2',5'-Dihydroxyacetophenone(490-78-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: AM7700000
• TSCA: Yes
• Hazardous Substances Data: 490-78-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow to yellow-green crystals or

Uses

Different sources of media describe the Uses of 490-78-8 differently. You can refer to the following data:
1. 2',5'-Dihydroxyacetophenone is an intermediate used in various synthetic preparations of pharmaceutical goods, 1-(2,5-Dihydroxyphenyl)ethanone was untilized in the synthesis of new flavonoid fatty acid esters with anti-adipogenic and glucose consumption enhancing activities.
2. 1-(2,5-Dihydroxyphenyl)ethanone is an intermediate used in various synthetic preparations of pharmaceutical goods, 1-(2,5-Dihydroxyphenyl)ethanone was untilized in the synthesis of new flavonoid fatty acid esters with anti-adipogenic and glucose consumption enhancing activities.

Preparation

Preparation by Fries rearrangement of hydroquinone diacetate,with aluminium chloride(91%) (76%)(63–77%) (55–60%)with zinc chloride in refluxing acetic acid (quantitative yield)with boron trifluoride etherate in benzene at reflux (65%).

Synthesis Reference(s)

The Journal of Organic Chemistry, 18, p. 1709, 1953 DOI: 10.1021/jo50018a014

Synthetic route

acetic acid (64-19-7) + hydroquinone (123-31-9) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With boron trifluoride diethyl etherate for 0.0333333h; microwave irradiation;	98%
With iron(III) chloride for 0.0166667h; Friedel Crafts acylation; Microwave irradiation; regioselective reaction;	98%
With aluminum oxide; methanesulfonic acid at 120℃; for 0.333333h;	85%

acetic anhydride (108-24-7) + hydroquinone (123-31-9) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
Stage #1: acetic anhydride; hydroquinone In 1,2-dichloro-ethane at 100℃; for 4h; Friedel-Crafts Acylation; Stage #2: With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 120℃; for 3h;	92%
zinc(II) chloride at 145 - 150℃; for 0.25h;	76%

2-oxo-propionic acid (127-17-3) + p-benzoquinone (106-51-4) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With ammonium persulfate; silver nitrate In water; acetonitrile at 70℃; for 2h;	92%

benzene-1,4-diyl diacetate (1205-91-0) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
for 0.116667h; Rearrangement; microwave irradiation;	90%
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 140 - 195℃; for 0.15h; Stage #2: With hydrogenchloride; water for 0.5h; Reflux;	85%
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 180℃; for 3h; Fries rearrangement; Stage #2: With hydrogenchloride In methanol Reflux;	76.6%

1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone (40815-75-6) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride In benzene for 20h; Heating;	89%

Dipropyl ether (111-43-3) + benzene-1,4-diyl diacetate (1205-91-0) → 2,5-Dihydroxyacetophenone (490-78-8) + 2-hydroxy-5-propoxyacetophenone (288074-68-0)

Conditions	Yield
With boron trifluoride for 1h; Fries rearrangement; Heating;	A 89% B 9%

1-(2-hydroxy-5-methoxyphenyl)ethan-1-one (705-15-7) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With pyridinium p-toluenesulfonate for 0.025h; microwave irradiation;	85%

(+)-euryfuran (67919-45-3) + 2-Acetyl-1,4-benzoquinone (1125-55-9) → 2,5-Dihydroxyacetophenone (490-78-8) + 2-acetyl-3-(6',6',9'a-trimethyl-4',5',5'aS,6',7',8',9',9'aS-octahydronaphtho[1,2-c]furan-3'-yl)-1,4-benzoquinone + 3,6-dihydroxy-2-(6',6',9'a-trimethyl-4',5',5'aS,6',7',8',9',9'aS-octahydronaphtho[1,2-c]furan-3'-yl)-acetophenone

Conditions	Yield
In dichloromethane at 20℃; for 5h; Michael reaction;	A n/a B 80% C 17%
In dichloromethane at 20℃; for 5h; Arylation;	A n/a B 51% C 17%

2-Acetyl-1,4-benzoquinone (1125-55-9) + trimethyl(2-methyl-2-propenyl)stannane (55562-82-8) → 2,5-Dihydroxyacetophenone (490-78-8) + 2-acetyl-3-(2-methylallyl)-1,4-benzenediol

Conditions	Yield
In benzene	A 6% B 77%

2',5'-dimethoxyacetophenone (1201-38-3) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With boron dimethyl-trifluoro sulphide In dichloromethane at 20℃; for 1.5h;	74%
With carbon disulfide; aluminum tri-bromide
With pyridine hydrochloride

4-methoxyphenyl acetate (1200-06-2) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With aluminium trichloride at 140℃; for 2h; Fries rearrangement;	71%
Fries rearrangement;

acetyl chloride (75-36-5) + hydroquinone (123-31-9) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With zinc at 47 - 48℃; for 0.0166667h; Friedel-Crafts acylation; microwave irradiation;	70%
With aluminium trichloride; nitrobenzene

hydroquinone (123-31-9) + Phenyl acetate (122-79-2) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 3h; crossover Friess rearrangement; Heating;	65%

5'-cinnamyloxy-2'-hydroxyacetophenone (79950-56-4) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
at 220℃; for 20h;	64%

2',5'-dimethoxyacetophenone (1201-38-3) → 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one (705-15-7) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With boron dimethyl-trifluoro sulphide In dichloromethane at 0℃; for 0.166667h;	A 64% B 27%

2-Acetyl-1,4-benzoquinone (1125-55-9) → 2-Acetyl-3-(3-acetyl-4-hydroxyphenoxy)-1,4-benzoquinone (68157-88-0) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With rose bengal In acetonitrile for 8h; Irradiation; Yields of byproduct given;	A 60% B n/a

benzene-1,4-diyl diacetate (1205-91-0) + phenol (108-95-2) → o-hydroxyacetophenone (118-93-4) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;	A 25% B 60%

2-Acetyl-1,4-benzoquinone (1125-55-9) → 5-hydroxy-2,3-dihydrobenzofuran-3-one (19278-82-1) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
In benzene for 72h; Irradiation;	A 50% B 45%
In benzene for 72h; Mechanism; Irradiation;	A 50% B 45%

α-naphthol (90-15-3) + benzene-1,4-diyl diacetate (1205-91-0) → 1-hydroxy-2-acetonaphthone (711-79-5) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;	A 20% B 50%

benzene-1,4-diyl diacetate (1205-91-0) + β-naphthol (135-19-3) → 1-(2-hydroxy-1-naphthyl)ethan-1-one (574-19-6) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;	A 35% B 45%

3,5-dihydroxyphenol (108-73-6) + benzene-1,4-diyl diacetate (1205-91-0) → 2,4,6-trihydroxyacetophenone (480-66-0) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;	A 35% B 40%

2-Acetyl-1,4-benzoquinone (1125-55-9) + trimethyl(allyl)stannane (762-73-2) → 2-acetyl-3-prop-2'-enyl-1,4-hydroquinone (40815-79-0) + 2,5-Dihydroxyacetophenone (490-78-8) + 3a-acetyl-2-trimethylstannyl-2,3,3a,4,7,7a-hexahydrindene-4,7-dione

Conditions	Yield
In benzene for 5h;	A 27% B 36% C 23%
In benzene dissolved acylquinone and allylstannane stood for 5 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.;	A 27% B 36% C 23%

benzene-1,4-diyl diacetate (1205-91-0) → 1,4-diacetyl-2,5-dihydroxybenzene (20129-52-6) + 5'-Acetoxy-2'-hydroxyacetophenone (21222-04-8) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
In methanol for 12h; Irradiation;	A 10% B 15% C 35%

acetophenone (98-86-2) → 3-Hydroxyacetophenone (121-71-1) + 2,3,6-trihydroxyacetophenone (85918-30-5) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -35℃; for 0.5h; Mechanism; Product distribution;	A 31% B 4% C 18%
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -35℃; for 0.5h;	A 31% B 4% C 18%

4a,8a-cis-4a-acetyl-4a,5,8,8a-tetrahydro-5,8-methano-1,4-naphthoquinone (75925-74-5, 94842-18-9) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With pyridine In xylene Heating;	29%

(1R,4S)-4a-Acetyl-1,4,4a,8a-tetrahydro-1,4-methano-naphthalene-5,8-dione → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
In pyridine; xylene at 120℃; for 3h;	29%

2-Acetyl-1,4-benzoquinone (1125-55-9) + allyltributylstanane (24850-33-7) → 2-acetyl-3-prop-2'-enyl-1,4-hydroquinone (40815-79-0) + 2,5-Dihydroxyacetophenone (490-78-8) + 3a-acetyl-2-tributylstannyl-2,3,3a,4,7,7a-hexahydrindene-4,7-dione

Conditions	Yield
In benzene for 1.5h;	A 29% B 10% C 10%
In benzene dissolved acylquinone and allylstannane stood for 1.5 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.;	A 29% B 10% C 10%

2-acetylcyclohexanone (874-23-7) → 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With (Z/E)-2-bromo-2-[4-oxothiazolidin-2-ylidene]-N-phenylacetamide; dimethyl sulfoxide for 3h; Reflux;	19%

2-Acetyl-1,4-benzoquinone (1125-55-9) + trimethyl(allyl)stannane (762-73-2) → 2-acetyl-3-prop-2'-enyl-1,4-hydroquinone (40815-79-0) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
In acetonitrile dissolved acylquinone and allylstannane stood for 10 min under Ar; concentrated; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.;	A 18% B 18%

benzene-1,4-diyl diacetate (1205-91-0) → 5'-Acetoxy-2'-hydroxyacetophenone (21222-04-8) + 2,5-Dihydroxyacetophenone (490-78-8)

Conditions	Yield
With aluminium trichloride at 190 - 200℃;
Stage #1: benzene-1,4-diyl diacetate With aluminium trichloride; sodium chloride at 195℃; for 0.15h; Fries rearrangement; Stage #2: With hydrogenchloride In water for 12h; Further stages. Title compound not separated from byproducts.;
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 140 - 195℃; for 0.15h; Stage #2: With hydrogenchloride; water

ethyl (E)-4-methyl-3,5-hexadienoate (76200-27-6) + 2,5-Dihydroxyacetophenone (490-78-8) → (4aR,5R,8aS)-4a-Acetyl-5-(2-benzyloxy-ethyl)-6-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone (72826-95-0, 80866-98-4)

Conditions	Yield
With silver(l) oxide Ambient temperature; Absence of light;	100%

C13H18O4 (134637-25-5) + 2,5-Dihydroxyacetophenone (490-78-8) → C21H24O7 (134637-35-7)

Conditions	Yield
With silver(l) oxide Ambient temperature;	100%

C14H20O4 (134637-27-7) + 2,5-Dihydroxyacetophenone (490-78-8) → C22H26O7 (134637-38-0)

Conditions	Yield
With silver(l) oxide Ambient temperature;	100%

C15H20O5 (134685-78-2) + 2,5-Dihydroxyacetophenone (490-78-8) → C23H26O8 (134637-30-2)

Conditions	Yield
With silver(l) oxide for 72h; Ambient temperature;	100%

C16H22O5 (134637-20-0) + 2,5-Dihydroxyacetophenone (490-78-8) → C24H28O8 (134637-32-4)

Conditions	Yield
With silver(l) oxide for 168h; Ambient temperature;	100%

3,4-dihydro-2H-pyran (110-87-2) + 2,5-Dihydroxyacetophenone (490-78-8) → 1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one (3557-22-0)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃;	99%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4h;	91%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 5h;	87%

benzyl bromide (100-39-0) + 2,5-Dihydroxyacetophenone (490-78-8) → 1-[2',5'-bis(phenylmethoxy)phenyl]ethanone (21766-81-4)

Conditions	Yield
With potassium carbonate In acetone for 18h; Etherification; Heating;	99%
With potassium carbonate In acetone for 24h; Reflux;	94%
Stage #1: 2,5-Dihydroxyacetophenone In 1,2-dimethoxyethane at 80℃; Inert atmosphere; Stage #2: benzyl bromide In 1,2-dimethoxyethane; N,N-dimethyl-formamide for 12h;	93%

cycl-isopropylidene malonate (2033-24-1) + 2,5-Dihydroxyacetophenone (490-78-8) → 6-hydroxy-4-methyl-2-oxo-2H-chromene-3-carboxylic acid

Conditions	Yield
With kiwi juice In water at 20℃; for 0.0833333h; Reagent/catalyst; Knoevenagel Condensation; Sonication; Green chemistry;	99%
With lithium perchlorate for 0.0194444h; Irradiation;	83%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 2,5-Dihydroxyacetophenone (490-78-8) → (2-(1-(trimethylsilyloxy)vinyl)-1,4-phenylene)bis(oxy)bis(trimethylsilane)

Conditions	Yield
With triethylamine In dichloromethane at -30 - -10℃; for 0.666667h; Inert atmosphere; Sealed tube;	99%

methyl chloroformate (79-22-1) + 2,5-Dihydroxyacetophenone (490-78-8) → Carbonic acid 3-acetyl-4-methoxycarbonyloxy-phenyl ester methyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran 0 deg C to room temp., 0.5 to 1 h;	98%

2,5-Dihydroxyacetophenone (490-78-8) + isoprene (78-79-5) → (4aR,8aS)-4a-Acetyl-7-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone

Conditions	Yield
With lithium perchlorate; acetic acid In nitromethane for 16h; electrolysis;	97%

tert-butyldimethylsilyl chloride (18162-48-6) + 2,5-Dihydroxyacetophenone (490-78-8) → 5'-t-butyldimethylsilyloxy-2'-hydroxyacetophenone (843644-58-6)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h;	97%

o-hydroxyacetophenone (118-93-4) + 2,5-Dihydroxyacetophenone (490-78-8) → tert-butyl 4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate (849928-22-9)

Conditions	Yield
With pyrrolidine In methanol for 24h;	97%

allyl bromide (106-95-6) + 2,5-Dihydroxyacetophenone (490-78-8) → 1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone (40815-75-6)

Conditions	Yield
With potassium carbonate In acetone for 18h; Heating;	96%
With potassium carbonate; sodium iodide In acetone for 15h; Heating;	86%
With potassium carbonate In acetone for 18h; Inert atmosphere; Reflux;	86%

2,5-Dihydroxyacetophenone (490-78-8) → 2-Acetyl-1,4-benzoquinone (1125-55-9)

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 0.25h; Ambient temperature;	95%
With oxygen In chloroform; water at 20℃; under 760.051 Torr; for 6h;	88%
With cerium(IV) ammonium nitrate; silica gel In dichloromethane for 0.25h;	84%

benzyl bromide (100-39-0) + 2,5-Dihydroxyacetophenone (490-78-8) → 5-benzyloxy-2-hydroxyacetophenone (30992-63-3)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate; potassium iodide In toluene at 115℃; for 14h;	95%
With potassium carbonate In acetone for 48h; Reflux;	92%
With sodium hydrogencarbonate In ethanol at 0 - 10℃; for 3.33333h;	88.3%

ethylene glycol (107-21-1) + 2,5-Dihydroxyacetophenone (490-78-8) → acetylhydroquinone ethylene acetal

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 24h; Heating;	95%

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8) + 2,5-Dihydroxyacetophenone (490-78-8) → 6-Hydroxy-2-methyl-2-((3E,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-chroman-4-one (150035-61-3)

Conditions	Yield
With pyrrolidine; 3 A molecular sieve In ethanol Heating;	95%

pivaloyl chloride (3282-30-2) + 2,5-Dihydroxyacetophenone (490-78-8) → 2,2-dimethylpropanoic acid 2-acetyl-1,4-phenylene ester (309721-51-5)

Conditions	Yield
With pyridine at 20℃;	95%
With pyridine at 20℃; for 18h;

orthoformic acid triethyl ester (122-51-0) + 2,5-Dihydroxyacetophenone (490-78-8) → 6-hydroxy-4-oxo-4H-1-benzopyran (38445-24-8)

Conditions	Yield
With perchloric acid In water at 20 - 100℃; for 1.08333h;	95%
With perchloric acid at 20℃; for 1.5h;	78%

1-adamanthanol (768-95-6) + 2,5-Dihydroxyacetophenone (490-78-8) → 2',5'-dihydroxy-3'-(1-adamantyl)acetophenone

Conditions	Yield
With sulfuric acid In dichloromethane at 0℃; Inert atmosphere; Reflux;	94.9%

2,5-Dihydroxyacetophenone (490-78-8) → 2-bromo-1-(2,5-dihydroxyphenyl)ethanone (25015-91-2)

Conditions	Yield
With aluminium trichloride; Montmorillonite K10; bromine In ethyl acetate at 20℃; for 2h;	94%
With urea-hydrogen peroxide; acetic acid; sodium bromide; silica gel at 120 - 122℃; for 0.00611111h; microwave irradiation;	71%
With copper(I) bromide In chloroform; ethyl acetate for 6h; Reflux;	6%

tert-butyldimethylsilyl chloride (18162-48-6) + 2,5-Dihydroxyacetophenone (490-78-8) → 1-(2,5-bis(tert-butyldimethylsilyloxy)phenyl)ethanone (1431642-68-0)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere;	93.2%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + 2,5-Dihydroxyacetophenone (490-78-8) → tert-butyl 6-hydroxy-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (911227-48-0)

Conditions	Yield
With pyrrolidine In methanol at 60℃; for 48h;	93%
With pyrrolidine In methanol for 18h; Reflux;	87%
With pyrrolidine In methanol for 23h; Reflux;	82%

6-Methyl-hept-5-en-2-on (110-93-0) + 2,5-Dihydroxyacetophenone (490-78-8) → 6-Hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-4-chromanon (69367-11-9)

Conditions	Yield
With pyrrolidine; 3 A molecular sieve In ethanol Heating;	92%

2,5-Dihydroxyacetophenone (490-78-8) + benzylamine (100-46-9) → 2,5-Dihydroxyphenylethylidenebenzylamine (82488-61-7)

Conditions	Yield
In toluene Heating; or ZnCl2, 1) 30 min, 160 deg C, 2) 5 min, 180 deg C;	92%
In toluene Heating;	90%

cyclohexanone (108-94-1) + 2,5-Dihydroxyacetophenone (490-78-8) → 6-hydroxy-spiro-4-one (135110-68-8)

Conditions	Yield
With piperidine for 0.166667h; Neat (no solvent); Microwave irradiation;	92%
With pyrrolidine In ethanol Reflux;	92%
With Amberlite IRA 400 basic resin for 0.133333h; Microwave irradiation; Neat (no solvent);	86%
With pyrrolidine In isopropyl alcohol for 2h; Mechanism; Heating; other acetophenones;	72%
With pyrrolidine In isopropyl alcohol for 2h; Heating;	72%

Upstream product

• 50-80-6 5-amino-2-hydroxyacetophenone 
• 75-07-0 acetaldehyde 
• 106-51-4 p-benzoquinone 
• 64-19-7 acetic acid 
• 123-31-9 hydroquinone 
• 75-36-5 acetyl chloride 
• 1205-91-0 benzene-1,4-diyl diacetate 
• 1125-55-9 2-Acetyl-1,4-benzoquinone 
• 75-05-8 acetonitrile 
• 127-17-3 2-oxo-propionic acid 
• 122-79-2 Phenyl acetate 
• 7446-70-0 aluminium trichloride 
• 1200-06-2 4-methoxyphenyl acetate 
• 69788-77-8 1-acetoxy-4-ethoxy-benzene 

Downstream Products

• 30992-63-3 5-benzyloxy-2-hydroxyacetophenone 
• 21766-81-4 1-[2',5'-bis(phenylmethoxy)phenyl]ethanone 
• 6342-92-3 2',5'-dihydroxy-4-methoxychalcone 
• 76323-08-5 1-acetyl-1,3-bis(benzoyloxy)benzene 
• 61429-74-1 6-hydroxy-2-(3-hydroxyphenyl)chroman-4-one 
• 35794-88-8 6‐hydroxy‐4′‐methoxyflavone 
• 40815-75-6 1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone 
• 137502-80-8 6-hydroxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 
• 38445-24-8 6-hydroxy-4H-1-benzopyran-4-one 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 1125-55-9 2-Acetyl-1,4-benzoquinone 
• 30095-74-0 2,5-dihydroxy-3-nitroacetophenone 
• 58344-57-3 2',5'-dihydroxy-3,4-methylenedioxy-trans-chalcone 
• 33857-20-4 1-(3-bromo-2,5-dihydroxy-phenyl)-ethanone 

Relevant articles and documents

(1,5)-Acetyl Shifts in Cycloadducts derived from 2-Acetyl-1,4-benzoquinones

(1,5)-Acetyl shifts have been investigated in a number of cycloadducts prepared from 2-acetyl-1,4-benzoquinone and dienes, and it has been shown that the direction of migration depends on the nature of the diene substituents.

Synthesis and pharmacological evaluation of acylhydroquinone derivatives as potent antiplatelet agents

Platelets are the smallest blood cells, and their activation (platelet cohesion or aggregation) at sites of vascular injury is essential for thrombus formation. Since the use of antiplatelet therapy is an unsolved problem, there are now focused and innovative efforts to develop novel antiplatelet compounds. In this context, we assessed the antiplatelet effect of an acylhydroquinone series, synthesized by Fries rearrangement under microwave irradiation, evaluating the effect of diverse acyl chain lengths, their chlorinated derivatives, and their dimethylated derivatives both in the aromatic ring and also the effect of the introduction of a bromine atom at the terminus of the acyl chain. Findings from a primary screening of cytotoxic activity on platelets by lactate dehydrogenase assay identified 19 non-toxic compounds from the 27 acylhydroquinones evaluated. A large number of them showed IC50 values less than 10 μM acting against specific pathways of platelet aggregation. The highest activity was obtained with compound 38, it exhibited sub-micromolar IC50 of 0.98 ± 0.40, 1.10 ± 0.26, 3.98 ± 0.46, 6.79 ± 3.02 and 42.01 ± 3.48 μM against convulxin-, collagen-, TRAP-6-, PMA- and arachidonic acid-induced platelet aggregation, respectively. It also inhibited P-selectin and granulophysin expression. We demonstrated that the antiplatelet mechanism of compound 38 was through a decrease in a central target in human platelet activation as in mitochondrial function, and this could modulate a lower response of platelets to activating agonists. The results of this study show that the chemical space around ortho-carbonyl hydroquinone moiety is a rich source of biologically active compounds, signaling that the acylhydroquinone scaffold has a promising role in antiplatelet drug research.

Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones

American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.