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150-19-6

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150-19-6 Usage

Chemical Properties

Clear pink red liquid

Uses

Different sources of media describe the Uses of 150-19-6 differently. You can refer to the following data:
1. A phenol derivative, 3-Methoxyphenol can be used as catalysts and as building blocks in synthesis of organic compounds such as antioxidants.
2. 3-Methoxyphenol may be used as an analytical standard for the determination of the analyte in wine, coffee beans, wood samples, and mainstream smoke by gas chromatography (GC) based techniques.

Preparation

synthesis of 3-methoxyphenol: The 1 mole of resorcinol is treated rapidly with stirring, in a three-necked flask provided with a reflux condenser, stirrer, internal thermometer, and dropping funnel, with 1.25 mole of 10% sodium hydroxide. With vigorous stirring, 1 mole of dimethyl sulfate is added in such a way that the temperature remains below 40° C (water cooling). To complete the reaction and to destroy unchanged dimethyl sulfate, the mixture is then heated for 30 min on a boiling water bath. After cooling, the organic layer is separated off and the aqueous solution is extracted several times with ether. The combined organic phases are washed with dilute sodium carbonate and then with water, dried with calcium chloride, and fractionated. Unchanged resorcinol can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 3-methoxyphenol is 50%, b.p. 113-115 °C/5 mm; b.p. 144°C/25mm; n20/D 1.552; d=1.131 g/mL at 25 °C. Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 206-207, (1973)

Definition

ChEBI: 3-methoxyphenol is a member of the class of phenols that is phenol having a methoxy-substituent at the 3-position. It is a member of phenols and a monomethoxybenzene. It derives from a resorcinol.

General Description

3-Methoxyphenol is a phenolic aroma compound typically present in food and beverage products.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. Human systemic effects by inhalation: muscle weakness, headache, and irritabdtty. Human female reproductive effects by inhalation: menstrual cycle changes and dsorders. A severe eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHERS.

Check Digit Verification of cas no

The CAS Registry Mumber 150-19-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 0 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 150-19:
(5*1)+(4*5)+(3*0)+(2*1)+(1*9)=36
36 % 10 = 6
So 150-19-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O2.C2H6O/c7-5-2-1-3-6(8)4-5;1-3-2/h1-4,7-8H;1-2H3

150-19-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A12826)  3-Methoxyphenol, 97%   

  • 150-19-6

  • 25g

  • 328.0CNY

  • Detail
  • Alfa Aesar

  • (A12826)  3-Methoxyphenol, 97%   

  • 150-19-6

  • 100g

  • 908.0CNY

  • Detail
  • Alfa Aesar

  • (A12826)  3-Methoxyphenol, 97%   

  • 150-19-6

  • 500g

  • 3834.0CNY

  • Detail

150-19-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-methoxyphenol

1.2 Other means of identification

Product number -
Other names m-Hydroxyanisole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:150-19-6 SDS

150-19-6Synthetic route

3-methoxybenzenediazonium tetrafluoroborate

3-methoxybenzenediazonium tetrafluoroborate

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With water Heating;100%
3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry;99%
With pyrene-1,6-dione; oxygen; isopropyl alcohol at 20℃; under 760.051 Torr; for 40h; Irradiation; Green chemistry;98%
With C18H28Cl2CuN2O4 In water at 26℃; for 0.333333h;96%
C13H23NOSi

C13H23NOSi

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol; water at 20℃; for 16h; Inert atmosphere;99%
3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 24h;99%
With copper(I) oxide; water; potassium carbonate; Sucrose at 140℃; for 18h; Sealed tube; Inert atmosphere;92%
With copper(l) iodide; triethanolamine; tetrabutylammomium bromide; water; potassium hydroxide at 120℃; for 24h; Inert atmosphere;89%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone; sodium hexamethyldisilazane In tetrahydrofuran at 185℃; for 12h; further reagent: LDA;98%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline In diethyl ether; xylene at 120℃; for 6.5h;95%
With lithium thioethoxide In N,N-dimethyl-formamide at 135℃; for 0.25h; Inert atmosphere; Microwave irradiation;90%
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1.5h;98%
With copper(I) oxide; tetra(n-butyl)ammonium hydroxide; 1,10-phenanthroline-4,7-diol In water at 110℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;96%
With copper(l) iodide; potassium hydroxide In water at 120℃; for 12h; Inert atmosphere;90%
dimethyl sulfate
77-78-1

dimethyl sulfate

recorcinol
108-46-3

recorcinol

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; Solvent;96.8%
With sodium hydrogencarbonate at 50℃; for 1h; Williamson synthesis;80%
With sodium hydrogencarbonate at 60℃; for 1h;79%
acetic acid 3-methoxyphenyl ester
5451-83-2

acetic acid 3-methoxyphenyl ester

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With silica-supported phosphomolybdic acid In methanol at 20℃; for 2h;96%
With potassium carbonate In methanol at 20℃;50%
With methanol; potassium carbonate at 20℃;50%
3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;96%
C10H12O4

C10H12O4

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 1h;95%
3-benzyloxyanisole
21144-16-1

3-benzyloxyanisole

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 60℃; for 4h; Inert atmosphere;94%
With sodium In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 2h;92%
With 1,3-dimethyl-2-imidazolidinone; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 185℃; for 12h;91%
3-allyloxyanisole
37592-19-1

3-allyloxyanisole

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 0 - 35℃; Hydrolysis;94%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 20℃; for 4h; Inert atmosphere;93%
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 0℃;87%
methanol
67-56-1

methanol

3-monochlorophenol
108-43-0

3-monochlorophenol

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
Irradiation;94%
Mechanism; Irradiation; other substituted phenols, other nucleophiles, competition reaction with methanol and N-methylacetamide;94%
methanol
67-56-1

methanol

3-fluorophenol
372-20-3

3-fluorophenol

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
Irradiation;94%
1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxybenzene
62790-77-6

1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxybenzene

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With potassium fluoride; hydrogen bromide In N,N-dimethyl-formamide at 25℃; for 2h;93%
potassium 3-methoxyphenyltrifluoroborate

potassium 3-methoxyphenyltrifluoroborate

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With Oxone; water In acetone at 20℃; for 0.0333333h;93%
With caesium carbonate; toluene-4-sulfonic acid hydrazide at 120℃; for 16h;85%
2-Cyclohexenyl-m-anisylether
72540-74-0

2-Cyclohexenyl-m-anisylether

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide; water at 30℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;93%
2-(5-methoxyphenoxy)-ethanol
34114-37-9

2-(5-methoxyphenoxy)-ethanol

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;92%
m-Anisidine
536-90-3

m-Anisidine

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
Stage #1: m-Anisidine With sulfuric acid at 20℃; Cooling with ice;
Stage #2: With sodium nitrite In water Reflux;
91%
Stage #1: m-Anisidine With tetrafluoroboric acid In water at 20℃; for 0.0333333h;
Stage #2: With sodium nitrite In water at 0℃; for 0.5h;
Stage #3: With copper(I) oxide; copper(II) sulfate In water at 0 - 20℃; for 0.5h;
66%
m-methoxyphenyl 2-propynyl ether
41580-72-7

m-methoxyphenyl 2-propynyl ether

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 20℃; for 0.25h;90%
1-methoxy-3-vinyloxybenzene
10536-50-2

1-methoxy-3-vinyloxybenzene

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide; water at 30℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;90%
With acetic acid In water for 0.5h; Reflux;90%
With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); water; bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide at 30℃; for 24h; Schlenk technique;87%
1-(but-3-enyloxy)-3-methoxybenzene
104886-22-8

1-(but-3-enyloxy)-3-methoxybenzene

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); water; bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide at 30℃; for 24h; Schlenk technique;90%
With 6,6'-dimethyl-2,2'-bipyridine; (1,2-dimethoxyethane)dichloronickel(II); bis(pinacol)diborane; lithium tert-butoxide In methanol; N,N-dimethyl acetamide; water at 30℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;90%
3-hydroxy-2-(4-methoxyphenoxy)-1-(3-methoxyphenyl)propan-1-one

3-hydroxy-2-(4-methoxyphenoxy)-1-(3-methoxyphenyl)propan-1-one

A

O-methylresorcine
150-19-6

O-methylresorcine

B

2-methoxy-1,4-benzoquinone
2880-58-2

2-methoxy-1,4-benzoquinone

C

3-methoxyphenyl 3-hydroxy-2-(4-methoxyphenoxy)propanoate

3-methoxyphenyl 3-hydroxy-2-(4-methoxyphenoxy)propanoate

Conditions
ConditionsYield
With methanesulfonic acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 6h; Flow reactor; Green chemistry;A 3%
B 86%
C 10%
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

A

O-methylresorcine
150-19-6

O-methylresorcine

B

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
With hydrogen iodide at 25℃; for 24h; Inert atmosphere;A 12%
B 85%
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave;A 50%
B 43%
3-methoxyphenyl benzenesulfonate
3753-53-5

3-methoxyphenyl benzenesulfonate

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere;85%
2-(3-methoxyphenoxy)-1-(3-methoxyphenyl)propane-1,3-diol

2-(3-methoxyphenoxy)-1-(3-methoxyphenyl)propane-1,3-diol

A

O-methylresorcine
150-19-6

O-methylresorcine

B

3-Methoxybenzoic acid
586-38-9

3-Methoxybenzoic acid

Conditions
ConditionsYield
With oxygen; sodium t-butanolate In tert-butyl alcohol at 30℃; under 760.051 Torr; for 16h; Green chemistry; chemoselective reaction;A 85%
B 95 %Spectr.
1-chloro-3-methoxy-benzene
2845-89-8

1-chloro-3-methoxy-benzene

O-methylresorcine
150-19-6

O-methylresorcine

Conditions
ConditionsYield
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; tris-(dibenzylideneacetone)dipalladium(0); cesiumhydroxide monohydrate In 1,4-dioxane at 110℃; Inert atmosphere; Glovebox; Sealed tube;84%
Stage #1: 1-chloro-3-methoxy-benzene With copper(l) iodide; 8-Hydroxyquinoline-N-oxide In dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With cesiumhydroxide monohydrate In water; dimethyl sulfoxide for 24h; Inert atmosphere; Reflux;
69%
2-(3-methoxyphenoxy)-1-(4-methoxyphenyl)propane-1,3-diol

2-(3-methoxyphenoxy)-1-(4-methoxyphenyl)propane-1,3-diol

A

O-methylresorcine
150-19-6

O-methylresorcine

B

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
ConditionsYield
With oxygen; sodium t-butanolate In tert-butyl alcohol at 30℃; under 760.051 Torr; for 16h; Green chemistry; chemoselective reaction;A 84%
B 89 %Spectr.
3-hydroxy-2-(2-methoxyphenoxy)-1-(3-methoxyphenyl)propan-1-one

3-hydroxy-2-(2-methoxyphenoxy)-1-(3-methoxyphenyl)propan-1-one

A

O-methylresorcine
150-19-6

O-methylresorcine

B

2-methoxy-1,4-benzoquinone
2880-58-2

2-methoxy-1,4-benzoquinone

C

3-methoxyphenyl 3-hydroxy-2-(2-methoxyphenoxy)propanoate

3-methoxyphenyl 3-hydroxy-2-(2-methoxyphenoxy)propanoate

Conditions
ConditionsYield
With methanesulfonic acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 6h; Flow reactor; Green chemistry;A 3%
B 84%
C 11%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

O-methylresorcine
150-19-6

O-methylresorcine

1-methoxy-3-tetrahydropyran-2-yloxybenzene
30778-86-0

1-methoxy-3-tetrahydropyran-2-yloxybenzene

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 1h; Ambient temperature;100%
With toluene-4-sulfonic acid In tetrahydrofuran at 0℃; for 0.25h;98%
With basic resin Amberlite IRA-400 (iodide form) In dichloromethane at 20℃; for 0.0833333h;92%
O-methylresorcine
150-19-6

O-methylresorcine

ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

4-(chloromethyl)-7-methoxy-2H-chromen-2-one
41295-55-0

4-(chloromethyl)-7-methoxy-2H-chromen-2-one

Conditions
ConditionsYield
With methanesulfonic acid at 20℃;100%
With silica gel supported zirconyl chloride octahydrate at 90℃; for 0.5h; Pechmann condensation reaction;96%
With perchloric acid; sulfuric acid at 25℃;95.2%
O-methylresorcine
150-19-6

O-methylresorcine

2-bromo-5-methoxyphenol
63604-94-4

2-bromo-5-methoxyphenol

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 4h; Heating;100%
With N-Bromosuccinimide In dichloromethane at 20℃; for 2h;98%
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate; potassium bromide In acetonitrile for 3.5h; Reflux; chemoselective reaction;96%
O-methylresorcine
150-19-6

O-methylresorcine

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

1-methoxy-3-(trimethylsiloxy)benzene
33285-71-1

1-methoxy-3-(trimethylsiloxy)benzene

Conditions
ConditionsYield
at 80℃; for 3h; Inert atmosphere;100%
With Nafion SAC-13 at 20℃; for 0.0833333h;98%
In nitromethane at 20℃; for 0.25h;95%
O-methylresorcine
150-19-6

O-methylresorcine

benzyl bromide
100-39-0

benzyl bromide

3-benzyloxyanisole
21144-16-1

3-benzyloxyanisole

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux; Sealed tube;100%
With potassium carbonate In acetonitrile for 12h; Reflux;91%
With potassium carbonate In acetonitrile Reflux;87%
O-methylresorcine
150-19-6

O-methylresorcine

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

3-methoxyphenyl triflate
66107-33-3

3-methoxyphenyl triflate

Conditions
ConditionsYield
Stage #1: O-methylresorcine With pyridine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique;
100%
With pyridine In dichloromethane at 0℃; for 0.333333h;97%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;93%
O-methylresorcine
150-19-6

O-methylresorcine

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
95715-87-0

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
925703-63-5

tert-butyl (R)-4-((R)-hydroxy(2-hydroxy-4-methoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: O-methylresorcine With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In dichloromethane at 0 - 20℃; for 15h;
100%
O-methylresorcine
150-19-6

O-methylresorcine

4-bromomethyl-4-(4-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

4-bromomethyl-4-(4-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

4-(4-bromo-phenyl)-4-(3-methoxy-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester
917899-09-3

4-(4-bromo-phenyl)-4-(3-methoxy-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 50 - 100℃; for 28h;100%
O-methylresorcine
150-19-6

O-methylresorcine

2-bromoaniline
615-36-1

2-bromoaniline

C21H20N3O2Pol

C21H20N3O2Pol

Conditions
ConditionsYield
With pyridine; copper(I) bromide dimethylsulfide complex; sodium carbonate In acetonitrile at 75℃; for 48h; Inert atmosphere; solid phase reaction;100%
O-methylresorcine
150-19-6

O-methylresorcine

3-chloro-4-fluoronitrobenzene
350-30-1

3-chloro-4-fluoronitrobenzene

2-chloro-1-(3-methoxyphenoxy)-4-nitrobenzene
708238-38-4

2-chloro-1-(3-methoxyphenoxy)-4-nitrobenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;100%
With potassium hydroxide In acetonitrile at 40℃;81.9%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;
O-methylresorcine
150-19-6

O-methylresorcine

4-methoxymethoxy-2-naphthalencarboxylic acid

4-methoxymethoxy-2-naphthalencarboxylic acid

C20H18O5

C20H18O5

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;100%
O-methylresorcine
150-19-6

O-methylresorcine

1-Bromopinacolon
5469-26-1

1-Bromopinacolon

1-(3-methoxyphenoxy)-3,3-dimethylbutan-2-one
39489-42-4

1-(3-methoxyphenoxy)-3,3-dimethylbutan-2-one

Conditions
ConditionsYield
With potassium carbonate In acetone at 70℃; for 16h;99%
With potassium carbonate
O-methylresorcine
150-19-6

O-methylresorcine

nitropentafluoroacetone
3888-00-4

nitropentafluoroacetone

2-(2,2-Difluoro-1-hydroxy-2-nitro-1-trifluoromethyl-ethyl)-5-methoxy-phenol
123716-14-3

2-(2,2-Difluoro-1-hydroxy-2-nitro-1-trifluoromethyl-ethyl)-5-methoxy-phenol

Conditions
ConditionsYield
In tetrachloromethane at 20℃; for 12h;99%
O-methylresorcine
150-19-6

O-methylresorcine

decafluorobiphenyl
434-90-2

decafluorobiphenyl

p,p'-bis(3-methoxyphenoxy)octafluorobiphenyl
85225-65-6

p,p'-bis(3-methoxyphenoxy)octafluorobiphenyl

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6h;99%
O-methylresorcine
150-19-6

O-methylresorcine

4-fluorobenzonitrile
1194-02-1

4-fluorobenzonitrile

4-(3’-methoxyphenoxy)benzonitrile
148291-60-5

4-(3’-methoxyphenoxy)benzonitrile

Conditions
ConditionsYield
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 72h; Heating;99%
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 72h; Heating;99%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 18h;98%
With caesium carbonate In N,N-dimethyl-formamide for 24h; Reflux;78%
O-methylresorcine
150-19-6

O-methylresorcine

2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

2-(3-methoxyphenoxy)benzonitrile
135199-38-1

2-(3-methoxyphenoxy)benzonitrile

Conditions
ConditionsYield
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 72h; Heating;99%
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 72h; Heating;99%
O-methylresorcine
150-19-6

O-methylresorcine

2-fluoro-6-methoxybenzonitrile
94088-46-7

2-fluoro-6-methoxybenzonitrile

2-Methoxy-6-(3-methoxy-phenoxy)-benzonitrile

2-Methoxy-6-(3-methoxy-phenoxy)-benzonitrile

Conditions
ConditionsYield
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 36h; Heating;99%
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 36h; Heating;99%
O-methylresorcine
150-19-6

O-methylresorcine

2-fluoro-6-[(4-methylphenyl)sulfanyl]benzonitrile
175204-11-2

2-fluoro-6-[(4-methylphenyl)sulfanyl]benzonitrile

2-(3-Methoxy-phenoxy)-6-p-tolylsulfanyl-benzonitrile

2-(3-Methoxy-phenoxy)-6-p-tolylsulfanyl-benzonitrile

Conditions
ConditionsYield
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 18h; Heating;99%
O-methylresorcine
150-19-6

O-methylresorcine

propargyl bromide
106-96-7

propargyl bromide

m-methoxyphenyl 2-propynyl ether
41580-72-7

m-methoxyphenyl 2-propynyl ether

Conditions
ConditionsYield
In acetone; toluene at 20℃;99%
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; for 7h; Inert atmosphere;97%
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; for 7h; Inert atmosphere;97%
O-methylresorcine
150-19-6

O-methylresorcine

2-fluoro-6-[(4-methylthio)phenoxy]benzonitrile

2-fluoro-6-[(4-methylthio)phenoxy]benzonitrile

2-(3-Methoxy-phenoxy)-6-(4-methylsulfanyl-phenoxy)-benzonitrile

2-(3-Methoxy-phenoxy)-6-(4-methylsulfanyl-phenoxy)-benzonitrile

Conditions
ConditionsYield
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 18h; Heating;99%
O-methylresorcine
150-19-6

O-methylresorcine

1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

1-bromo-2-((3-methoxyphenoxy)methyl)benzene
309254-29-3

1-bromo-2-((3-methoxyphenoxy)methyl)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃;99%
Stage #1: O-methylresorcine With sodium hydride In tetrahydrofuran for 0.5h; Metallation; Heating;
Stage #2: 1-Bromo-2-bromomethyl-benzene In tetrahydrofuran for 4h; Etherification; Heating; Further stages.;
97%
O-methylresorcine
150-19-6

O-methylresorcine

iodobenzene
591-50-4

iodobenzene

1-methoxy-3-phenoxybenzene
1655-68-1

1-methoxy-3-phenoxybenzene

Conditions
ConditionsYield
With 2,2,6,6-tetramethylheptane-3,5-dione; iron(III) chloride; caesium carbonate In N,N-dimethyl-formamide at 135℃; for 20h;99%
With copper(II) glycinate monohydrate; potassium hydroxide In dimethyl sulfoxide at 80℃; for 8h; Ullmann reaction;92%
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 18h; Inert atmosphere;89%
O-methylresorcine
150-19-6

O-methylresorcine

1-(diphenylmethyl)-1H-indole-2,3-dione
94878-41-8

1-(diphenylmethyl)-1H-indole-2,3-dione

1-(diphenylmethyl)-3-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one
1019771-93-7

1-(diphenylmethyl)-3-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

Conditions
ConditionsYield
Stage #1: O-methylresorcine With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.75h;
Stage #2: 1-(diphenylmethyl)-1H-indole-2,3-dione In dichloromethane at 0 - 20℃; for 16h;
99%
O-methylresorcine
150-19-6

O-methylresorcine

ethyl 2-oxocyclohexane carboxylate
1655-07-8

ethyl 2-oxocyclohexane carboxylate

3-methoxy-7,8,9,10-tetrahydro-6H-dibenzopyran-6-one
54245-26-0

3-methoxy-7,8,9,10-tetrahydro-6H-dibenzopyran-6-one

Conditions
ConditionsYield
In trifluoroacetic acid at 100℃; for 0.5h; Pechmann reaction; microwave irradiation;99%
O-methylresorcine
150-19-6

O-methylresorcine

diphenyliodonium tetrafluoroborate

diphenyliodonium tetrafluoroborate

1-methoxy-3-phenoxybenzene
1655-68-1

1-methoxy-3-phenoxybenzene

Conditions
ConditionsYield
Stage #1: O-methylresorcine With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h;
Stage #2: diphenyliodonium tetrafluoroborate In tetrahydrofuran at 20℃; for 3h;
99%

150-19-6Relevant articles and documents

Synthesis of coumarins via palladium-catalyzed carbonylative annulation of internal alkynes by o-lodophenols

Kadnikov, Dmitry V.,Larock, Richard C.

, p. 3643 - 3646 (2000)

(matrix presented) A variety of substituted coumarins have been prepared in good yields by the palladium-catalyzed coupling of o-iodophenols with internal alkynes and 1 atm of carbon monoxide. Unlike most of the previous work on the palladium-catalyzed carbonylation of alkynes, the insertion of the internal alkyne occurs in preference to the insertion of CO.

Selective production of methoxyphenols from dihydroxybenzenes on alkali metal ion-loaded MgO

Vijayaraj, Munusamy,Gopinath, Chinnakonda S.

, p. 376 - 388 (2006)

Selective O-methylation of dihydroxybenzenes (DHBs; catechol, resorcinol, and hydroquinone) to methoxyphenols (MPs) was carried out with dimethylcarbonate on MgO and alkali metal ion (Li, K, and Cs)-loaded MgO between 523 and 603 K. Catalytic activity and product selectivity varied with respect to DHB substrates. Selectivity for O-methylated products increased with increasing basicity of alkali ions; however, K-MgO showed high and stable activity toward MPs. Selectivity for MPs obtained from three substrates increased in the following order: catechol 2 followed by air and 13C CP-MAS NMR measurements indicated the nature of deposited carbon to be molecular species, graphite, MgCO3 and polyaromatics. XPS revealed the nature and availability of active sites on the spent catalysts, as well as the same changes with reaction conditions and correlated with catalytic activity.

Imidazolium-urea low transition temperature mixtures for the UHP-promoted oxidation of boron compounds

Martos, Mario,Pastor, Isidro M.

, (2022/01/03)

Different carboxy-functionalized imidazolium salts have been considered as components of low transition temperature mixtures (LTTMs) in combination with urea. Among them, a novel LTTM based on 1-(methoxycarbonyl)methyl-3-methylimidazolium chloride and urea has been prepared and characterized by differential scanning calorimetry throughout its entire composition range. This LTTM has been employed for the oxidation of boron reagents using urea-hydrogen peroxide adduct (UHP) as the oxidizer, thus avoiding the use of aqueous H2O2, which is dangerous to handle. This metal-free protocol affords the corresponding alcohols in good to quantitative yields in up to 5 mmol scale without the need of further purification. The broad composition range of the LTTM allows for the reaction to be carried out up to three consecutive times with a single imidazolium salt loading offering remarkable sustainability with an E-factor of 7.9, which can be reduced to 3.2 by the threefold reuse of the system.

Catalyst-free rapid conversion of arylboronic acids to phenols under green condition

Dong, Zhenhua,Liu, Mengmeng,Pan, Hongguo

, (2021/09/06)

A catalyst-free and solvent-free method for the oxidative hydroxylation of aryl boronic acids to corresponding phenols with hydrogen peroxide as the oxidizing agent was developed. The reactions could be performed under green condition at room temperature within very short reaction time. 99% yield of phenol could be achieved in only 1 min. A series of different arenes substituted aryl boronic acids were further carried out in the hydroxylation reaction with excellent yield. It was worth nothing that the reaction could completed within 1 min in all cases in the presence of ethanol as co-solvent.

Cu2O/TiO2 as a sustainable and recyclable photocatalyst for gram-scale synthesis of phenols in water

Hosseini-Sarvari, Mona,Keshavarz, Kimia,Tavakolian, Mina

, (2021/08/30)

A green and straightforward protocol was developed for the synthesis of phenols from aryl boronic acid using an inexpensive and available Cu2O/TiO2 photocatalyst under visible light and sunlight. This approach proceeded in mild reaction conditions in water and the presence of air as a green oxidant, resulting in the corresponding phenols in good to excellent yields. Sunlight was also a sustainable source for this photochemical reaction. Heterogeneous nano photocatalyst was successfully recovered in 8 consecutive runs. It is noteworthy that, the photocatalyst exhibited high activity for the large-scale synthesis of phenols.

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