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3555-86-0 Usage

Definition

ChEBI: A benzenetriol that is benzophenone in which one of the phenyl groups is substituted at by hydroxy groups at positions 2, 4, and 6.

Preparation

Preparation by Fries rearrangement of phloroglucinol tribenzoate with aluminium chloride at 160–170° for 2 h (95%).

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 6734, 1967 DOI: 10.1021/ja01001a060Tetrahedron, 26, p. 5255, 1970 DOI: 10.1016/S0040-4020(01)98735-6
InChI:InChI=1/C13H10O4/c14-9-6-10(15)12(11(16)7-9)13(17)8-4-2-1-3-5-8/h1-7,14-16H

3555-86-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,4,6-trihydroxybenzophenone

1.2 Other means of identification

Product number -
Other names benzoylphloroglucinol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3555-86-0 SDS

3555-86-0Synthetic route

2,4,6-trimethoxybenzophenone
3770-80-7

2,4,6-trimethoxybenzophenone

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78 - 20℃; for 74h; Inert atmosphere; Schlenk technique;100%
With boron tribromide In dichloromethane at -78 - 20℃; for 20h;99%
With boron tribromide In dichloromethane at -78 - 20℃;99%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

benzoyl chloride
98-88-4

benzoyl chloride

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With aluminum (III) chloride In nitrobenzene at 65℃; for 3h; Inert atmosphere;72%
With aluminum (III) chloride In nitrobenzene at 65℃; Friedel-Crafts Acylation;65.8%
Stage #1: 3,5-dihydroxyphenol With aluminum (III) chloride In carbon disulfide; nitrobenzene at 55℃; for 0.5h; Friedel-Crafts Acylation;
Stage #2: benzoyl chloride In carbon disulfide; nitrobenzene for 0.5h; Friedel-Crafts Acylation; Heating;
54%
2,4,6-trimethoxybenzophenone
3770-80-7

2,4,6-trimethoxybenzophenone

A

cotoin
479-21-0

cotoin

B

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Stage #1: 2,4,6-trimethoxybenzophenone With boron tribromide In dichloromethane at -78 - 20℃; for 48h; Inert atmosphere;
Stage #2: With water In dichloromethane at 0 - 20℃; for 1.3h;
A 4%
B 52%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

1,4-dibenzoyloxybenzene
14210-97-0

1,4-dibenzoyloxybenzene

A

2,5-dihydroxybenzophenone
2050-37-5

2,5-dihydroxybenzophenone

B

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation;A 50%
B 40%
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

benzoic acid phenyl ester
93-99-2

benzoic acid phenyl ester

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In benzene for 3h; crossover Friess rearrangement; Heating;25%
2-(α-phenylimino-benzyl)-phloroglucinol

2-(α-phenylimino-benzyl)-phloroglucinol

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With hydrogenchloride
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

benzonitrile
100-47-0

benzonitrile

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether; zinc(II) chloride Erhitzen des Reaktionsprodukts mit Wasser;
With diethyl ether
With hydrogenchloride; diethyl ether; zinc(II) chloride Man verwandelt das ausgeschiedene Ketimidhydrochlorid in das Sulfat und kocht dieses mit der 20-fachen Menge Wasser; Ausbeute 65prozent der Theorie;
7-Phenyl-3,5,7-trioxoheptansaeuremethylester
15148-46-6

7-Phenyl-3,5,7-trioxoheptansaeuremethylester

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With sodium hydroxide at -5℃;
4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one
20851-38-1

4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With lithium hydride
2,4,6-trihydroxy-benzophenone-imine; hydrochloride

2,4,6-trihydroxy-benzophenone-imine; hydrochloride

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With water for 1.5h; Heating;
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / AlCl3 / CH2Cl2 / 12 h / 0 - 20 °C
2: 92 percent / boron tribromide / CH2Cl2 / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 7.5 g / AlCl3 / diethyl ether / 15 h / Ambient temperature
2: 5.1 g / HI / acetic anhydride / 4 h / 115 - 120 °C
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere
1.2: 48 h / 20 °C / Inert atmosphere
2.1: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere
2.2: 1.3 h / 0 - 20 °C
View Scheme
benzoyl chloride
98-88-4

benzoyl chloride

(η-2,5-Ph2C4H2N)(Ph3P)2ReH2

(η-2,5-Ph2C4H2N)(Ph3P)2ReH2

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / AlCl3 / CH2Cl2 / 12 h / 0 - 20 °C
2: 92 percent / boron tribromide / CH2Cl2 / -78 - 20 °C
View Scheme
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ZnCl2; HCl / diethyl ether
2: H2O / 1.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: AlCl3; diethyl ether
2: ethanolic HCl
View Scheme
benzoyl chloride
98-88-4

benzoyl chloride

O5-benzoyl-O1,O2-isopropyliden-β-D-arabinofuranose

O5-benzoyl-O1,O2-isopropyliden-β-D-arabinofuranose

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 7.5 g / AlCl3 / diethyl ether / 15 h / Ambient temperature
2: 5.1 g / HI / acetic anhydride / 4 h / 115 - 120 °C
View Scheme
N-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3; diethyl ether
2: ethanolic HCl
View Scheme
1-phenylhexane-1,3,5-trione
1469-95-0

1-phenylhexane-1,3,5-trione

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) NaNH2, liq. NH3, Et2O, (ii) /BRN= 1900390/
2: diethyl ether
3: aq. NaOH / -5 °C
View Scheme
7-Phenyl-3,5,7-trioxo-heptansaeure
4809-02-3

7-Phenyl-3,5,7-trioxo-heptansaeure

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether
2: aq. NaOH / -5 °C
View Scheme
acide 2,4,6-trihydroxybenzoique
83-30-7

acide 2,4,6-trihydroxybenzoique

benzene
71-43-2

benzene

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With zinc(II) chloride; trichlorophosphate at 70℃; for 2.5h; Friedel-Crafts reaction;
Stage #1: acide 2,4,6-trihydroxybenzoique; benzene With zinc(II) chloride; trichlorophosphate at 70℃; for 2.5h;
Stage #2: With water at 4℃; for 24h; Cooling with ice;
benzoyl chloride
98-88-4

benzoyl chloride

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere
1.2: 48 h / 20 °C / Inert atmosphere
2.1: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere
2.2: 1.3 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C
1.2: 12 h / 0 - 20 °C
2.1: boron tribromide / dichloromethane / 20 h / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere; Schlenk technique
1.2: 16 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
2.1: boron tribromide / dichloromethane / 74 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C
1.2: 0 - 20 °C
2.1: boron tribromide / dichloromethane / -78 - 20 °C
View Scheme
<2-14C>malonyl-CoA

<2-14C>malonyl-CoA

S-benzoyl coenzyme A
6756-74-7

S-benzoyl coenzyme A

A

4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one
20851-38-1

4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one

B

4-hydroxy-6-phenyl-2H-pyran-2-one
5526-38-5

4-hydroxy-6-phenyl-2H-pyran-2-one

C

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With acridone synthase from Citrus Microcarpa pH=6.5 - 8.5; Enzymatic reaction;
S-benzoyl coenzyme A
6756-74-7

S-benzoyl coenzyme A

S-(hydrogen malonyl)coenzyme A
524-14-1

S-(hydrogen malonyl)coenzyme A

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

Conditions
ConditionsYield
With recombinant type III polyketide synthase from Aquilaria sinensis In aq. phosphate buffer at 37℃; for 12h; pH=7.0; Enzymatic reaction;
UDP-glucose
133-89-1

UDP-glucose

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

phlorobenzophenone 3-C-β-D-glucoside

phlorobenzophenone 3-C-β-D-glucoside

Conditions
ConditionsYield
With C-glycosyltransferase from Mangifera indica In methanol at 40℃; for 12h; pH=6.6; Enzymatic reaction;100%
With Mangifera indica C-glycosyltransferase for 12h; Enzymatic reaction; stereospecific reaction;4.5 mg
3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

6-benzoyl-5-hydroxy-2,8-dimethyl-2,8-bis(4-methylpent-3-enyl)-2H,8H-benzo(1,2-b:3',4'-b')dipyran

6-benzoyl-5-hydroxy-2,8-dimethyl-2,8-bis(4-methylpent-3-enyl)-2H,8H-benzo(1,2-b:3',4'-b')dipyran

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; for 36h;95%
3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

6-benzoyl-5-hydroxy-2,2,8,8-tetramethyl-2H,8H-benzo(1,2-b:3',4'-b')dipyran
88662-01-5

6-benzoyl-5-hydroxy-2,2,8,8-tetramethyl-2H,8H-benzo(1,2-b:3',4'-b')dipyran

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; for 36h;94%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

2-benzylidene-indan-1,3-dione
5381-33-9

2-benzylidene-indan-1,3-dione

2-((3-benzoyl-2,4,6-trihydroxy-5-((3-hydroxy-1-oxo-1H-inden-2-yl)(phenyl)methyl)phenyl)(phenyl)methyl)-3-hydroxy-1H-inden-1-one

2-((3-benzoyl-2,4,6-trihydroxy-5-((3-hydroxy-1-oxo-1H-inden-2-yl)(phenyl)methyl)phenyl)(phenyl)methyl)-3-hydroxy-1H-inden-1-one

Conditions
ConditionsYield
Stage #1: 2-benzoylphloroglucinol With sodium hydride In tetrahydrofuran for 0.166667h; Inert atmosphere;
Stage #2: 2-benzylidene-indan-1,3-dione In tetrahydrofuran for 1h;
92%
With sodium hydride In tetrahydrofuran at 20℃; Michael Addition;643 mg
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3-benzoyl-2,4,6-trihydroxy-benzaldehyde

3-benzoyl-2,4,6-trihydroxy-benzaldehyde

Conditions
ConditionsYield
With trichlorophosphate In ethyl acetate at 20℃; Inert atmosphere;91%
With trichlorophosphate In ethyl acetate79%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

2-(2-methylpropylidene)-1H-indene-1,3(2H)-dione
22123-54-2

2-(2-methylpropylidene)-1H-indene-1,3(2H)-dione

2-(1-(3-benzoyl-2,4,6-trihydroxy-5-(1-(3-hydroxy-1-oxo-1H-inden-2-yl)-2-methylpropyl)phenyl)-2-methylpropyl)-3-hydroxy-1H-inden-1-one

2-(1-(3-benzoyl-2,4,6-trihydroxy-5-(1-(3-hydroxy-1-oxo-1H-inden-2-yl)-2-methylpropyl)phenyl)-2-methylpropyl)-3-hydroxy-1H-inden-1-one

Conditions
ConditionsYield
Stage #1: 2-benzoylphloroglucinol With sodium hydride In tetrahydrofuran for 0.166667h; Inert atmosphere;
Stage #2: 2-(2-methylpropylidene)-1H-indene-1,3(2H)-dione In tetrahydrofuran for 1h;
77%
With sodium hydride In tetrahydrofuran at 20℃; Michael Addition;486 mg
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

acetic acid
64-19-7

acetic acid

2-acetyl-4-benzoylphloroglucinol
31188-65-5

2-acetyl-4-benzoylphloroglucinol

Conditions
ConditionsYield
With boron trifluoride76%
trans-geranyl bromide
6138-90-5

trans-geranyl bromide

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

(E)-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)(phenyl)methanone
70219-87-3

(E)-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)(phenyl)methanone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;63%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

prenyl bromide
870-63-3

prenyl bromide

phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone
93796-20-4

phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;63%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;62%
bromethyl methyl ether
13057-17-5

bromethyl methyl ether

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)(phenyl)methanone

(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)(phenyl)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;60%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-phen-1-one

1-(2,4-bis((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)-2-phen-1-one

Conditions
ConditionsYield
Stage #1: 2-benzoylphloroglucinol With 1H-imidazole In acetone for 0.0833333h;
Stage #2: tert-butyldimethylsilyl chloride In acetone at 20℃; for 2h; regioselective reaction;
58%
geranyl diphosphate
763-10-0

geranyl diphosphate

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

A

(E)-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)(phenyl)methanone
70219-87-3

(E)-(3-(3,7-dimethylocta-2,6-dienyl)-2,4,6-trihydroxyphenyl)(phenyl)methanone

B

(E)-4-(3,7-dimethylocta-2,6-dienyloxy)-2,6-dihydroxybenzophenone

(E)-4-(3,7-dimethylocta-2,6-dienyloxy)-2,6-dihydroxybenzophenone

Conditions
ConditionsYield
With Aspergillus terreus aromatic prenyltransferase; calcium chloride In dimethyl sulfoxide; glycerol at 37℃; for 2h; pH=7.5; Enzymatic reaction;A 54.72%
B 0.62%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)(phenyl)methanone

(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)(phenyl)methanone

Conditions
ConditionsYield
Stage #1: 2-benzoylphloroglucinol With potassium carbonate In acetone at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: chloromethyl methyl ether In acetone at 20℃; for 1h; Inert atmosphere; Schlenk technique;
50%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

2-chloro-4-nitrophenyl β-D-xylopyranoside

2-chloro-4-nitrophenyl β-D-xylopyranoside

C18H18O8

C18H18O8

Conditions
ConditionsYield
With recombinant Streptomyces venezuelae ISP5230 GT1 Sv0189 glycosyltransferase; UDP In aq. phosphate buffer at 20℃; pH=7.0; Enzymatic reaction;50%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

isoprene
78-79-5

isoprene

A

8-Benzoyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran
63565-07-1

8-Benzoyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran

B

6-Benzoyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran
86606-14-6

6-Benzoyl-5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran

C

6-Benzoyl-5-hydroxy-2,2,8,8-tetramethyl-3,4,9,10-tetrahydro-2H,8H-benzo<1,2-b:3,4-b'>dipyran
83611-02-3

6-Benzoyl-5-hydroxy-2,2,8,8-tetramethyl-3,4,9,10-tetrahydro-2H,8H-benzo<1,2-b:3,4-b'>dipyran

Conditions
ConditionsYield
With phosphoric acid In xylene at 30 - 35℃; for 12h;A 30%
B 48%
C 7%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

prenyl bromide
870-63-3

prenyl bromide

A

phenyl(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)-phenyl)methanone
70219-84-0

phenyl(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)-phenyl)methanone

B

phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone
93796-20-4

phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 45℃; for 24h;A 48%
B 13%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

prenyl bromide
870-63-3

prenyl bromide

phenyl(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)-phenyl)methanone
70219-84-0

phenyl(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)-phenyl)methanone

Conditions
ConditionsYield
With potassium hydroxide at 0℃; for 2h;45%
With potassium hydroxide In water at 0℃; for 1.33h;34%
With potassium hydroxide In water at 0℃; for 1.33333h; Inert atmosphere;34%
C17H35S(1+)*BF4(1-)

C17H35S(1+)*BF4(1-)

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

A

2,6-dihydroxy-4-prenyloxybenzophenone
70219-83-9

2,6-dihydroxy-4-prenyloxybenzophenone

B

phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone
93796-20-4

phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 7h;A 10%
B 42%
geranyl bromide
6138-90-5

geranyl bromide

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

phenyl[3-(3,7-dimethyl-2,6-octadienyl)-2,4,6-trihydroxyphenyl]methanone
70219-87-3, 76015-48-0

phenyl[3-(3,7-dimethyl-2,6-octadienyl)-2,4,6-trihydroxyphenyl]methanone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h;42%
allyl iodid
556-56-9

allyl iodid

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

(3,5-diallyl-2,4,6-trihydroxyphenyl)(phenyl)methanone
1570098-55-3

(3,5-diallyl-2,4,6-trihydroxyphenyl)(phenyl)methanone

Conditions
ConditionsYield
Stage #1: 2-benzoylphloroglucinol With potassium hydroxide In water at 20℃; Inert atmosphere;
Stage #2: allyl iodid In water at 20 - 60℃; for 0.666667h; Inert atmosphere;
Stage #3: With 1.3-propanedithiol In water at 60℃; for 0.0833333h; Inert atmosphere;
36%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

ethyl propanoylacetate
4949-44-4

ethyl propanoylacetate

6-benzoyl-4-ethyl-5,7-dihydroxy-2H-chromen-2-one
1313524-58-1

6-benzoyl-4-ethyl-5,7-dihydroxy-2H-chromen-2-one

Conditions
ConditionsYield
With sulfuric acid; acetic acid at 20℃; for 2h; Pechmann reaction;27%
3,7-dimethyl-2,6-octadienal
141-27-5

3,7-dimethyl-2,6-octadienal

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

A

[5,7-dihydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-1-benzopyran-6-yl]phenylmethanone
933983-29-0

[5,7-dihydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-1-benzopyran-6-yl]phenylmethanone

B

[5,7-dihydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-1-benzopyran-8-yl]phenylmethanone
933997-22-9, 163634-65-9

[5,7-dihydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-1-benzopyran-8-yl]phenylmethanone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 0℃; for 6h;A 11%
B 26%
dimethylallyl diphosphate
358-72-5

dimethylallyl diphosphate

2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

A

C23H26O4

C23H26O4

B

phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone
93796-20-4

phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone

Conditions
ConditionsYield
With Aspergillus terreus aromatic prenyltransferase; calcium chloride In dimethyl sulfoxide; glycerol at 37℃; for 2h; pH=7.5; Enzymatic reaction;A 5.29%
B 22.06%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

allyl bromide
106-95-6

allyl bromide

(3,5-diallyl-2,4,6-trihydroxyphenyl)(phenyl)methanone
1570098-55-3

(3,5-diallyl-2,4,6-trihydroxyphenyl)(phenyl)methanone

Conditions
ConditionsYield
With potassium hydroxide In water at 0 - 20℃; for 1.33333h; Inert atmosphere;22%
2-benzoylphloroglucinol
3555-86-0

2-benzoylphloroglucinol

ethyl 3-oxo-3-phenylpropionate
94-02-0

ethyl 3-oxo-3-phenylpropionate

6-benzoyl-5,7-dihydroxy-4-phenyl-2H-chromen-2-one
213834-81-2

6-benzoyl-5,7-dihydroxy-4-phenyl-2H-chromen-2-one

Conditions
ConditionsYield
With sulfuric acid; acetic acid In nitrobenzene at 20℃; for 2h; Pechmann reaction;15%
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