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2,5-Dihydro-2,5-dimethoxyfuran is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 332-77-4 Structure
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    1. Product Name: 2,5-Dihydro-2,5-dimethoxyfuran
    2. Synonyms: 2,5-DIHYDRO-2,5-DIMETHOXYFURAN;2,5-DIHYDRO-2,5-DIMETHOXFURAN;2,5-DIMETHOXY-2,5-DIHYDROFURAN;2,5-DIMETHOXY-2,5-DIHYDROFURAN, 97%, MIXTURE OF CIS AND TRANS;2,5-Dihydro-2,5-dimethoxyfurane;Furan, 2,5-dihydro-2,5-dimethoxy-;2,5-dihydro-2,5-dimethoxyfuran, cis + trans;2,5-DIHYDRO-2,5-DIMETHOXYFURAN, CIS + TRANS 99%
    3. CAS NO:332-77-4
    4. Molecular Formula: C6H10O3
    5. Molecular Weight: 130.14
    6. EINECS: 206-367-5
    7. Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Furan&Benzofuran;Furans;Pharmaceutical;Building Blocks;C4 to C7;Chemical Synthesis;Heterocyclic Building Blocks
    8. Mol File: 332-77-4.mol
  • Chemical Properties

    1. Melting Point: <-40°C
    2. Boiling Point: 160-162 °C(lit.)
    3. Flash Point: 117 °F
    4. Appearance: Clear/Liquid
    5. Density: 1.073 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 3.02mmHg at 25°C
    7. Refractive Index: n20/D 1.434(lit.)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: 368g/l
    10. Explosive Limit: 1.1-18.3%(V)
    11. BRN: 113225
    12. CAS DataBase Reference: 2,5-Dihydro-2,5-dimethoxyfuran(CAS DataBase Reference)
    13. NIST Chemistry Reference: 2,5-Dihydro-2,5-dimethoxyfuran(332-77-4)
    14. EPA Substance Registry System: 2,5-Dihydro-2,5-dimethoxyfuran(332-77-4)
  • Safety Data

    1. Hazard Codes:  Xn:Harmful;
    2. Statements: 10
    3. Safety Statements: 16-29-33-24/25
    4. RIDADR: UN 1993 3/PG 3
    5. WGK Germany: 1
    6. RTECS:
    7. TSCA: Yes
    8. HazardClass: 3
    9. PackingGroup: III
    10. Hazardous Substances Data: 332-77-4(Hazardous Substances Data)

332-77-4 Usage

Chemical Properties

Colorless to light yellow liqui

Check Digit Verification of cas no

The CAS Registry Mumber 332-77-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,3 and 2 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 332-77:
(5*3)+(4*3)+(3*2)+(2*7)+(1*7)=54
54 % 10 = 4
So 332-77-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O3/c1-7-5-3-4-6(8-2)9-5/h3-6H,1-2H3/t5-,6-/m0/s1

332-77-4 Well-known Company Product Price

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  • Alfa Aesar

  • (B25028)  2,5-Dihydro-2,5-dimethoxyfuran, cis + trans, 99%   

  • 332-77-4

  • 50g

  • 426.0CNY

  • Detail
  • Alfa Aesar

  • (B25028)  2,5-Dihydro-2,5-dimethoxyfuran, cis + trans, 99%   

  • 332-77-4

  • 100g

  • 725.0CNY

  • Detail
  • Alfa Aesar

  • (B25028)  2,5-Dihydro-2,5-dimethoxyfuran, cis + trans, 99%   

  • 332-77-4

  • 250g

  • 1541.0CNY

  • Detail
  • Alfa Aesar

  • (B25028)  2,5-Dihydro-2,5-dimethoxyfuran, cis + trans, 99%   

  • 332-77-4

  • 500g

  • 2774.0CNY

  • Detail
  • Alfa Aesar

  • (B25028)  2,5-Dihydro-2,5-dimethoxyfuran, cis + trans, 99%   

  • 332-77-4

  • 1000g

  • 4986.0CNY

  • Detail
  • Aldrich

  • (D134104)  2,5-Dimethoxy-2,5-dihydrofuran,mixtureofcisandtrans  97%

  • 332-77-4

  • D134104-100G

  • 1,063.53CNY

  • Detail

332-77-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,5-dimethoxy-2,5-dihydrofuran

1.2 Other means of identification

Product number -
Other names 2,5-Dimethoxy-2,5-dihydrofuran

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:332-77-4 SDS

332-77-4Synthetic route

furan
110-00-9

furan

methanol
67-56-1

methanol

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

Conditions
ConditionsYield
With ammonium bromide at -22℃; for 7.5h; Electrochemical reaction;85%
With triethylmethylammonium chloride; sodium carbonate at -5 - 5℃; for 10h;85.3%
With tris(2,2'-bipyridyl)ruthenium dichloride at 20℃; under 760.051 Torr; Reagent/catalyst; Irradiation;82%
methanol
67-56-1

methanol

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

Conditions
ConditionsYield
Stage #1: methanol; 1,4-butenediol With tributylmethylammonium methanesulfonate; phosphoric acid at 22℃; for 19h; Electrolysis;
Stage #2: With sodium methylate In methanol pH=8 - 9;
46%
furan
110-00-9

furan

methanol
67-56-1

methanol

potassium acetate
127-08-2

potassium acetate

A

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

B

2-Acetoxy-5-methoxy-2,5-dihydro-furan
859303-52-9

2-Acetoxy-5-methoxy-2,5-dihydro-furan

Conditions
ConditionsYield
With bromine
furan
110-00-9

furan

methanol
67-56-1

methanol

bromine
7726-95-6

bromine

potassium acetate
127-08-2

potassium acetate

A

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

B

2-Acetoxy-5-methoxy-2,5-dihydro-furan
859303-52-9

2-Acetoxy-5-methoxy-2,5-dihydro-furan

furan
110-00-9

furan

methanol
67-56-1

methanol

ammonium bromide

ammonium bromide

A

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

B

1,1,4,4-tetramethoxy-2-butene
5370-08-1

1,1,4,4-tetramethoxy-2-butene

Conditions
ConditionsYield
Electrolysis;
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

3-(2-hydroxyphenyl)-3-oxopropanoate ethyl ester
23008-77-7

3-(2-hydroxyphenyl)-3-oxopropanoate ethyl ester

ethyl 2-(furan-2-yl)-3-(2-hydroxyphenyl)-3-oxopropanoate

ethyl 2-(furan-2-yl)-3-(2-hydroxyphenyl)-3-oxopropanoate

Conditions
ConditionsYield
With K10 Montmorillonite Clay In neat (no solvent) at 80℃; for 2h; Catalytic behavior; Solvent; Temperature; Green chemistry;96%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

(Carboxy-methoxy-methoxy)-methoxy-acetic acid

(Carboxy-methoxy-methoxy)-methoxy-acetic acid

Conditions
ConditionsYield
With potassium permanganate In potassium hydroxide for 2h;95%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

acrolein
107-02-8

acrolein

Conditions
ConditionsYield
With potassium permanganate In potassium hydroxide for 2.5h;95%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

ethyl 4-methoxybenzoylacetate
2881-83-6

ethyl 4-methoxybenzoylacetate

2-furan-2-yl-3-(4-methoxy-phenyl)-3-oxo-propionic acid ethyl ester
719311-02-1

2-furan-2-yl-3-(4-methoxy-phenyl)-3-oxo-propionic acid ethyl ester

Conditions
ConditionsYield
With zinc(II) chloride at 80℃;95%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

methyl 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
57595-95-6

methyl 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

carbomethoxy-2 (furyl-2)-2 dimethoxy-6,7 dihydro-3,4 naphtalenone-1
116672-79-8

carbomethoxy-2 (furyl-2)-2 dimethoxy-6,7 dihydro-3,4 naphtalenone-1

Conditions
ConditionsYield
With zinc(II) chloride In tetrahydrofuran; acetic acid for 1h; Heating;94%
With acetic acid; zinc(II) chloride In tetrahydrofuran Heating;90%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

diethyl malonate
105-53-3

diethyl malonate

α-(furan-2-yl) diethyl malonate
40572-09-6

α-(furan-2-yl) diethyl malonate

Conditions
ConditionsYield
Zinc chloride In water; acetic acid94%
methanol
67-56-1

methanol

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

C11H17NO4

C11H17NO4

Conditions
ConditionsYield
Stage #1: 2,5-dihydro-2,5-dimethoxyfuran; methyl (S)-allylglycinate With hydrogenchloride
Stage #2: methanol With sulfuric acid for 3h; Heating; Further stages.;
93%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

ethyl 3-(2-hydroxy-4,5-dimethoxyphenyl)-3-oxopropanoate

ethyl 3-(2-hydroxy-4,5-dimethoxyphenyl)-3-oxopropanoate

3-(furan-2-yl)-4-hydroxy-6,7-dimethoxy-2H-chromen-2-one

3-(furan-2-yl)-4-hydroxy-6,7-dimethoxy-2H-chromen-2-one

Conditions
ConditionsYield
Stage #1: 2,5-dihydro-2,5-dimethoxyfuran; ethyl 3-(2-hydroxy-4,5-dimethoxyphenyl)-3-oxopropanoate at 80℃; for 1h;
Stage #2: With sodium hydroxide In ethanol Temperature; Reflux;
93%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

(+/-)-8,9-dimethoxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one
33545-52-7

(+/-)-8,9-dimethoxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one

Conditions
ConditionsYield
With 1,2,3-Benzotriazole In acetic acid for 24h; Heating;92%
With acetic acid Heating;53%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

5-chloro-1H-indole
17422-32-1

5-chloro-1H-indole

C20H12Cl2N2

C20H12Cl2N2

Conditions
ConditionsYield
With 3-(1,1-dioxido-4-(3-(3-(3-sulfopropyl)-1H-imidazol-3-ium-1-yl)propyl)thiomorpholino-4-ium)propane-1-sulfonate trifluoromethanesulfonate In acetic acid butyl ester at 80℃; for 2h;92%
methanol
67-56-1

methanol

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

potassium methanolate
865-33-8

potassium methanolate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

A

Methyl formate
107-31-3

Methyl formate

B

1,1,4,4-tetramethoxy-2-butene
5370-08-1

1,1,4,4-tetramethoxy-2-butene

Conditions
ConditionsYield
Stage #1: methanol; 2,5-dihydro-2,5-dimethoxyfuran; trimethyl orthoformate; toluene-4-sulfonic acid under 760.051 Torr;
Stage #2: potassium methanolate With Pluriol E400 at 100 - 130℃; Product distribution / selectivity;
A n/a
B 91.3%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

ethyl 3-(2-hydroxy-4,6-dimethoxyphenyl)-3-oxopropanoate

ethyl 3-(2-hydroxy-4,6-dimethoxyphenyl)-3-oxopropanoate

3-(furan-2-yl)-4-hydroxy-5,7-dimethoxy-2H-chromen-2-one

3-(furan-2-yl)-4-hydroxy-5,7-dimethoxy-2H-chromen-2-one

Conditions
ConditionsYield
Stage #1: 2,5-dihydro-2,5-dimethoxyfuran; ethyl 3-(2-hydroxy-4,6-dimethoxyphenyl)-3-oxopropanoate at 80℃; for 1h;
Stage #2: With sodium hydroxide In ethanol Temperature; Reflux;
91%
1-methylindole
603-76-9

1-methylindole

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

C22H18N2

C22H18N2

Conditions
ConditionsYield
With 3-(1,1-dioxido-4-(3-(3-(3-sulfopropyl)-1H-imidazol-3-ium-1-yl)propyl)thiomorpholino-4-ium)propane-1-sulfonate trifluoromethanesulfonate In acetic acid butyl ester at 80℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent;91%
methanol
67-56-1

methanol

2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

methyl 4,4-dimethoxybutanoate
4220-66-0

methyl 4,4-dimethoxybutanoate

Conditions
ConditionsYield
(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) at 150℃; for 12h;90%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

methyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
40153-87-5

methyl 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

carbomethoxy-2 (furyl-2)-2 methoxy-6 dihydro-3,4 naphtalenone-1
116672-78-7

carbomethoxy-2 (furyl-2)-2 methoxy-6 dihydro-3,4 naphtalenone-1

Conditions
ConditionsYield
With acetic acid; zinc(II) chloride In tetrahydrofuran Heating;90%
With zinc(II) chloride In tetrahydrofuran; acetic acid for 1h; Heating;84%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
7442-52-6, 125117-36-4

methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

carbomethoxy-2 (furyl-2)-2 dihydro-3,4 naphtalenone-1
116672-77-6

carbomethoxy-2 (furyl-2)-2 dihydro-3,4 naphtalenone-1

Conditions
ConditionsYield
With acetic acid; zinc(II) chloride In tetrahydrofuran Heating;90%
With zinc(II) chloride In tetrahydrofuran; acetic acid for 1h; Heating;88%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

ethyl vinyl ether
109-92-2

ethyl vinyl ether

2-furylacetaldehyde diethyl acetal

2-furylacetaldehyde diethyl acetal

Conditions
ConditionsYield
With magnesium bromide In diethyl ether at 20℃; for 0.25h; Product distribution; Further Variations:; Reaction partners; reaction times;90%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

2-Benzofuranpropionic acid-β-oxo-ethylester
78917-44-9

2-Benzofuranpropionic acid-β-oxo-ethylester

ethyl 3-(benzofuran-2-yl)-2-(furan-2-yl)-3-oxopropanoate

ethyl 3-(benzofuran-2-yl)-2-(furan-2-yl)-3-oxopropanoate

Conditions
ConditionsYield
With K10 montmorillonite clay In hexane at 80℃; for 3h;90%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

ethyl 3-(2-hydroxy-6-methoxyphenyl)-3-oxopropanoate

ethyl 3-(2-hydroxy-6-methoxyphenyl)-3-oxopropanoate

3-(furan-2-yl)-4-hydroxy-5-methoxy-2H-chromen-2-one

3-(furan-2-yl)-4-hydroxy-5-methoxy-2H-chromen-2-one

Conditions
ConditionsYield
Stage #1: 2,5-dihydro-2,5-dimethoxyfuran; ethyl 3-(2-hydroxy-6-methoxyphenyl)-3-oxopropanoate at 80℃; for 1h;
Stage #2: With sodium hydroxide In ethanol Temperature; Reflux;
90%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

N-Ethylindole
10604-59-8

N-Ethylindole

C24H22N2

C24H22N2

Conditions
ConditionsYield
With 3-(1,1-dioxido-4-(3-(3-(3-sulfopropyl)-1H-imidazol-3-ium-1-yl)propyl)thiomorpholino-4-ium)propane-1-sulfonate trifluoromethanesulfonate In acetic acid butyl ester at 80℃; for 2h;90%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

N-butylindole
22014-99-9

N-butylindole

C28H30N2

C28H30N2

Conditions
ConditionsYield
With 3-(1,1-dioxido-4-(3-(3-(3-sulfopropyl)-1H-imidazol-3-ium-1-yl)propyl)thiomorpholino-4-ium)propane-1-sulfonate trifluoromethanesulfonate In acetic acid butyl ester at 80℃; for 2h;90%

332-77-4Relevant articles and documents

Electro-oxidation of hispanolone and anti-inflammatory properties of the obtained derivatives

Nieto-Mendoza, Elizabeth,Guevara-Salazar, Juan A.,Ramirez-Apan, Maria Teresa,Frontana-Uribe, Bernardo A.,Cogordan, Juan A.,Cardenas, Jorge

, p. 4538 - 4541 (2005)

The electrochemical oxidation ((+)Pt-Ni(-)/NH4Br/MeOH) of the natural product hispanolone (1a) produced, in high yield (>95%), spiro-tetracyclic compounds 7a-7d as a result of the intramolecular addition of the C-9 hydroxyl group into the C-16 position with the simultaneous addition of a CH3O group at the C-15 position of the hispanolone furan moiety. After the electrochemical oxidation, an acid-catalyzed slow secondary reaction occurred producing the previously undescribed α-butenolide derivative, iso-Leopersin G (9). An anti-inflammatory study with the electro-synthesized compounds showed that 1a has higher anti-inflammatory properties with very low cytotoxicity (e.g., the inhibition of TPA-induced ear edema assay IC 50 = 1.05 μM/ear, positive control indomethacin IC50 = 0.27 μM/ear).

Method of preparing 2,5-dimethoxy-2,5-dihydrofuran through biomass furan photocatalysis

-

Paragraph 0020-0039, (2020/02/20)

The invention discloses a method of preparing 2,5-dimethoxy-2,5-dihydrofuran through biomass furan photocatalysis. Currently, two traditional synthesis methods are available, wherein one is a chemicalsynthesis method which is implemented through a halogenation reaction between furan and elemental bromine, and the method is gradually eliminated because the reaction process is high in production cost and causes serious environmental pollution; and the other one is an electrolysis method, wherein the furan is subjected to electrolytic oxidation in a methanol solution, and the method has the defects that production cost is high, and electrolyte treatment is complicated. According to the method, biomass furan and methanol are used as raw materials, and the 2,5-dimethoxy-2,5-dihydrofuran is synthesized through a photocatalyst function in a room-temperature normal-pressure air atmosphere under visible light illumination. Through the method, operation is easy, production cost is greatly lowered, environmental pollution is avoided, and therefore the synthesis method has industrial development value and is efficient and environmentally friendly.

MANUFACTURING METHOD AND MANUFACTURING DEVICE FOR 2,5-DIALKOXY-2,5-DIHYDROFURAN OR THE LIKE

-

Paragraph 0026-0028; 0033; 0038; 0039, (2018/06/01)

PROBLEM TO BE SOLVED: To provide an efficient manufacturing method of 2,5-dialkoxy-2,5-dihydrofuran and/or a derivative from furan and/or a derivative thereof by photoelectrolytic oxidation using light energy. SOLUTION: There is provided a manufacturing method of 2,5-dialkoxy-2,5-dihydrofuran and/or a derivative by using a photoelectrolytic oxidation reaction for irradiating a light to a visible light-responsive photoanode electrode surface using furan represented by the formula (1) and/or a derivative thereof and alcohol represented by the formula (2). R1 and R2 are each independently H, a methyl group, an ethyl group or the like. R3OH (2), where R3 is an alkyl group of C4 or lower. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2018,JPOandINPIT

A 2, 5 - furan two alkoxyl dihydro preparation method of compound

-

Paragraph 0023; 0024, (2017/08/25)

The invention provides a preparation method of a 2,5-dialkoxyl dihydrofuran compound. The preparation method comprises the following steps: adding a furan compound shown by a formula I, alkyl alcohol shown by a formula III and an acid-binding agent into a reactor, stirring to react with chlorine, keeping the reaction temperature to be (-25)-25 DEG C, and reacting to obtain a 2,5-dialkoxyl dihydrofuran compound shown by a formula II, wherein in the formulas, R1, R2, R3 and R4 are independent hydrogen, halogen and C1-C5 alkyl, and R1 is a C1-C12 alkyl. The method provided by the invention is less in investment, low in energy consumption and high in efficiency; the reaction method is simple, and the operation is convenient and easy to implement; the raw materials are low in price, easy to obtain, and low in production cost; a byproduct is salt and can meet requirements on environmental protection; and the preparation method is suitable for performing industrial large-scale production of the 2,5-dialkoxyl dihydrofuran compound. Particularly, when a phase transfer catalyst is added into the method provided by the invention, the method also has the advantage that the yield of a target product is obviously improved.

A practical microreactor for electrochemistry in flow

Watts, Kevin,Gattrell, William,Wirth, Thomas

experimental part, p. 1108 - 1114 (2011/10/05)

A microreactor for electrochemical synthesis has been designed and fabricated. It has been shown that different reactions can be carried out successfully using simple protocols.

METHOD FOR PRODUCING ALKOXYLATED 2,5-DIHYDROFURAN BUT-2-ENE DERIVATIVES OR TETRA-1,1,4,4-ALKOXYLATED BUT-2-ENE DERIVATIVES

-

Page/Page column 9, (2008/06/13)

The invention relates to a method for producing 2,5-dihydrofuran derivatives that are substituted in position 3 or 4, which carry a respective C1 to C6 alkoxy group (DHF alkoxy derivates I) in position 2 or position 5, or in both positions, or for producing 1,1,4,4-tetraalkoxy but-2-ene derivatives that are substituted in position 3 or 4, from 2-butene-1,4-diol derivatives of general formula (I), in which the groups R1 and R2 independently of one another represent hydrogen, C1 to C6 alkyl, C6 to C12 aryl or C5 to C12 cycloalkene or R1 and R2 together with the double bond, to which they are linked, form a C6 to C12 aryl group or a mono- or polyunsaturated C5 to C12 cycloalkyl group, or from a mixture of said 2-butene-1,4-diol derivatives and 2,5-dihydrofuran derivatives that are substituted in position 3 or 4 and carry a C1 to C6 alkoxy group in position 2 or 5, by electrochemical oxidation in the presence of a C1 to C6 monoalkyl alcohol.

Development of a novel environmentally friendly electrolytic system by using recyclable solid-supported bases for in situ generation of a supporting electrolyte from methanol as a solvent: Application for Anodic methoxylation of organic compounds

Tajima, Toshiki,Fuchigami, Toshio

, p. 6192 - 6196 (2007/10/03)

We have successfully developed a novel environmentally friendly electrolytic system using recyclable solid-supported bases for in situ generation of a supporting electrolyte from methanol as a solvent. It was found that solid-supported bases are electrochemically inactive at an electrode surface. It was also found that solid-supported bases dissociate methanol into methoxide anions and protons. Therefore, in the presence of solid-supported bases, it was clarified that methanol serves as both a solvent and a supporting electrolyte generated in situ. Anodic methoxylation of various compounds with solid-supported bases was carried out to provide the corresponding methoxylated products in good to excellent yields with a few exceptions. The methoxylated products and the solid-supported bases were easily separated by only filtration, and the desired pure methoxylated products were readily isolated simply by concentration of the filtrates. The separated and recovered solid-supported bases were recyclable for several times.

Crenulacetal C, a marine diterpene, and its synthetic mimics inhibiting Polydora websterii, a harmful lugworm damaging pearl cultivation

Takikawa, Mami,Uno, Kiyoko,Ooi, Takashi,Kusumi, Takenori,Akera, Shusaku,Muramatsu, Morimitsu,Mega, Hirohiko,Horita, Chie

, p. 462 - 466 (2007/10/03)

Polydora websterii, a harmful lugworm that has serious adverse effects on pearl oyster cultivation, was inhibited by a marine diterpene, crenulacetal C, isolated from the brown alga Dictyota dichotoma. Based on consideration of the activity-structure relationship, several synthetic compounds having an aromatic moiety with a hydroxyalkyl chain were prepared. Bioassay using larvae of Polydora websterii as well as pearl oysters (Pinctada fucata martians) suggested that 1-(2-ferrule)-1-nonanol was the most promising inhibitor.

The binary reagent PhI(OAc)2-Mg(ClO4)2: a SET induced ring enlargement of furan derivatives into pyranones

De Mico,Margarita,Piancatelli

, p. 3553 - 3556 (2007/10/02)

The binary reagent PhI(OAc)2-Mg(ClO4)2 is very efficient for a high conversion of (2-furyl)-1-alcohols into puranones. The reaction mechanism can be explained in terms of a SET process, with the generation of a cation radical as key intermediate.

Concurrent Anodic Cyanation and Methoxylation of Methylated Furans. Oxidation Potential and Reactivity, and Stereochemical Control of Addition

Yoshida, Kunihisa,Fueno, Takayuki

, p. 229 - 240 (2007/10/02)

The potentiostatic electrooxidation of a series of methyl-substituted furans was performed in MeOH that contains NaCN at a Pt anode in a divided cell.In all instances, the 1,4-additions of cyano and/or methoxyl group(s) across the furan ring were achieved.Replacement of an aromatic hydrogen by a cyano group occured concurrently in some cases.The relative rates of cation radicals toward two different nucleophiles (CN- ion and the solvent MeOH) (or the MeO- ion as a result of the equilibrium between CN- ion and the solvent MeOH) at the electrode surface were determined from the yields of products by using the rate expressions of competitive reactions.There is a linear correlation between the relative reactivity of the furans (on a log scale) and their oxidation potential.The ratio of stereoisomers formed in an electrooxidation of 2,5-dimethylfuran (2,5-DMF) changes with addition of adsorbable compound as well as substrate concentration and this is thought to be due to the influence of concentration (or coadsorbate) on substrate orientation in the adsorption layer.

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