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

• 1205-91-0 benzene-1,4-diyl diacetate 
• 75-07-0 acetaldehyde 
• 106-51-4 p-benzoquinone 
• 64-19-7 acetic acid 
• 123-31-9 hydroquinone 
• 75-36-5 acetyl chloride 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 79950-56-4 5'-cinnamyloxy-2'-hydroxyacetophenone 
• 40815-75-6 1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone 
• 1125-55-9 2-Acetyl-1,4-benzoquinone 
• 24850-33-7 allyltributylstanane 
• 762-73-2 trimethyl(allyl)stannane 
• 55562-82-8 trimethyl(2-methyl-2-propenyl)stannane 
• 127-17-3 2-oxo-propionic acid 

Downstream Products

• 21222-04-8 5'-Acetoxy-2'-hydroxyacetophenone 
• 30992-63-3 5-benzyloxy-2-hydroxyacetophenone 
• 21766-81-4 1-[2',5'-bis(phenylmethoxy)phenyl]ethanone 
• 19312-14-2 (E)-1-(2,5-dihydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one 
• 76323-08-5 1-acetyl-1,3-bis(benzoyloxy)benzene 
• 61429-74-1 6-hydroxy-2-(3-hydroxyphenyl)chroman-4-one 
• 6665-83-4 6-hydroxyflavone 
• 40815-75-6 1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone 
• 108896-91-9 2',5'-dihydroxy-2-methoxy-trans-chalcone 
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• 685844-68-2 C₂₂H₁₄F₂O₅ 
• 131944-46-2 1-(2,5-Dihydroxy-phenyl)-3-(4-nitro-phenyl)-propane-1,3-dione 

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.

A chromone derivative as a colorimetric and “ON-OFF-ON” fluorescent probe for highly sensitive and selective detection of Cu2+ and S2?

A chromone derivative (L) which could be utilized for reversibly detecting Cu2+ and S2? by means of fluorescence quenching and displacement in aqueous solution was designed and developed. Upon the addition of Cu2+, the strong blue-green fluorescence emission of L was quenched rapidly and then recovered in 1 min by successively adding S2?. Furthermore, with the alternate addition of Cu2+ and S2?, the reversible cycles could be repeated for at least four times, which meant that L could be identified as a renewable dual-functioning probe. What's more, due to its excellent sensing performances, this probe L could also be used to detect Cu2+ and S2? with test strips conveniently.

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.