4-Hydroxy-6-methyl-2-pyrone

Base Information

• Chemical Name: 4-Hydroxy-6-methyl-2-pyrone
• CAS No.: 675-10-5
• Molecular Formula: C6H6O3
• Molecular Weight: 126.112
• Hs Code.: 29322980
• Mol file: 675-10-5.mol

Synonyms:2H-Pyran-2-one,4-hydroxy-6-methyl-;Sorbicacid, 3,5-dihydroxy-, d-lactone (6CI,7CI);Triacetic acid lactone;4-Hydroxy-6-methyl-2H-pyran-2-one;4-Hydroxy-6-methyl-a-pyrone;4-Hydroxy-6-methylpyran-2-one;6-Methyl-4-hydroxy-2-pyrone;NSC 34625;

Chemical Property of 4-Hydroxy-6-methyl-2-pyrone

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000311mmHg at 25°C
• Melting Point: 188-190 °C (dec.)(lit.)
• Refractive Index: 1.56
• Boiling Point: 239.074 °C at 760 mmHg
• PKA: 5.14±0.30(Predicted)
• Flash Point: 108.677 °C
• PSA: 50.44000
• Density: 1.348 g/cm³
• LogP: 0.65380
• Storage Temp.: Store below +30°C.
• Solubility.: 8.6g/l
• Water Solubility.: 8.60 g/L (20 ºC)

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxy-6-methylpyran-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 4-Hydroxy-6-methyl-2-pyrone is a heterocyclic compound that serves as a key intermediate in organic synthesis, particularly in the preparation of derivatives such as 4-amino-6-methyl-2H-pyran-2-one. It is also involved in azocoupling reactions with diazonium salts to form pyrazolylazo derivatives, demonstrating its versatility in the synthesis of heterocyclic compounds with potential applications in dyes and bioactive molecules. 4-Hydroxy-6-methyl-2-pyrone is a versatile heterocyclic intermediate used in the synthesis of amino-substituted pyran-2-one derivatives and participates in azocoupling reactions to form azo dyes and bioactive heterocycles. Its reactivity makes it valuable in organic and medicinal chemistry.

Technology Process of 4-Hydroxy-6-methyl-2-pyrone

There total 37 articles about 4-Hydroxy-6-methyl-2-pyrone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (771-03-9) → 4-hydroxy-6-methyl-2-pyron (675-10-5)

Guidance literature:

With sulfuric acid; In water; at 130 ℃; for 0.216667h; Flow reactor;

DOI:10.1002/ejoc.201600222

Reference yield: 94.0%

3,5-dioxohexanoic acid (2140-49-0) → 4-hydroxy-6-methyl-2-pyron (675-10-5)

Guidance literature:

With trifluoroacetic acid; trifluoroacetic anhydride; for 0.5h; Heating;

Reference yield: 92.0%

2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one (130473-38-0) → 4-hydroxy-6-methyl-2-pyron (675-10-5)

Guidance literature:

In toluene; at 100 ℃; for 0.5h;

DOI:10.3390/molecules24173193

upstream raw materials:

3,5-dioxohexanoic acid

phenyldiazomethane

4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-one

2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one

Downstream raw materials:

(E)-4-hydroxy-6-methyl-3-(3-phenylallyl)pyran-2-one

6-Methyl-4-((E)-3-phenyl-allyloxy)-pyran-2-one

3-<1-(4-Chlorphenyl)-3-oxo-butyl>-4-hydroxy-6-methyl-2H-pyran-2-on

2,7-dimethyl-2H,5H-pyrano<3,2-c>pyran-5-one

Refernces

4-AMINO-6-METHYL-2H-PYRAN-2-ONE. PREPARATION AND REACTIONS WITH AROMATIC ALDEHYDES.

10.1016/S0040-4020(01)90086-9

The research focuses on the synthesis of bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)arylmethanes (1). The key starting material is 4-amino-6-methyl-2H-pyran-2-one (10), which is synthesized from 4-hydroxy-6-methyl-2H-pyran-2-one (2) through a series of reactions. The researchers initially attempted to synthesize the target compounds by reacting arylbis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methanes (2) with ammonia, but this led to the formation of arylbis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)methanes (4) instead. To overcome this, they explored the use of a good leaving group at the C-4 position and eventually found that using 4-amino-6-methyl-2H-pyran-2-one (10) as a starting material was a feasible alternative. The synthesis involved condensation of 10 with various aromatic aldehydes under catalysis by p-toluenesulfonic acid in toluene, yielding the desired bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)arylmethanes (1). The study also involved the synthesis of several intermediate compounds, such as 4-azido-6-methyl-2H-pyran-2-one (12) and 1-(6-methyl-2-oxo-2H-pyran-4-yl)imidazole (14), using different reagents and conditions. The compounds were characterized by spectroscopic and analytical data, providing insights into their structures and properties.

Synthesis of new azocompounds and fused pyrazolo[5,1-c][1,2,4]triazines using heterocyclic components

10.1002/jhet.1533

The study, titled "Synthesis of New Azocompounds and Fused Pyrazolo[5,1-c][1,2,4]triazines Using Heterocyclic Components," investigates the synthesis of new azocompounds and tricyclic pyrazolo[5,1-c][1,2,4]triazines using various heterocyclic components. The key chemical involved is 3-methyl-4-phenyl-1H-pyrazol-5-amine, which is diazotized to form pyrazole-3(5)-diazonium chloride. This diazonium salt undergoes azocoupling reactions with a variety of heterocyclic compounds, including barbituric acid, thiobarbituric acid, 2-hetarylpyrimidine-4,6-diones, 4-hydroxy-6-methylpyridin-2(1H)-one, 4-hydroxy-6-methyl-2H-pyran-2-one, 4-hydroxy-1-p-tolyl-1H-pyrazole-3-carboxylic acid ethyl ester, 1,3-thiazolidine-2,4-dione, and 2-thioxo-1,3-thiazolidin-4-one. These reactions yield new pyrazolylazo derivatives and fused pyrazolo[5,1-c][1,2,4]triazines through subsequent heterocyclization processes. The study explores the synthetic potential of these heterocyclic components in azocoupling reactions, highlighting their potential applications in industrial azo dyes, analytical indicators, and bioactive compounds related to purines.