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| | 2,6-Dimethyl-4H-pyran-4-one Basic information |
| | 2,6-Dimethyl-4H-pyran-4-one Chemical Properties |
| Melting point | 133-137 °C(lit.) | | Boiling point | 248-250 °C(lit.) | | density | 0.9953 | | refractive index | 1.5300 (estimate) | | Fp | 248-250°C | | storage temp. | Sealed in dry,Room Temperature | | form | Crystalline Powder or Crystals | | color | White to beige | | Water Solubility | Slightly soluble in water. | | BRN | 107418 | | InChI | 1S/C7H8O2/c1-5-3-7(8)4-6(2)9-5/h3-4H,1-2H3 | | InChIKey | VSYFZULSKMFUJJ-UHFFFAOYSA-N | | SMILES | CC1=CC(=O)C=C(C)O1 | | LogP | 0.100 | | CAS DataBase Reference | 1004-36-0(CAS DataBase Reference) | | NIST Chemistry Reference | 4H-Pyran-4-one, 2,6-dimethyl-(1004-36-0) | | EPA Substance Registry System | 2,6-Dimethyl-4H-pyran-4-one (1004-36-0) |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 36/37 | | WGK Germany | 3 | | RTECS | UQ0780000 | | HS Code | 29329995 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | 2,6-Dimethyl-4H-pyran-4-one Usage And Synthesis |
| Chemical Properties | 2,6-Dimethyl-4H-pyran-4-one is white to beige crystalline powder or crystals | | Uses | 2,6-Dimethyl-4H-pyran-4-one is used as a fragrance ingredient. | | Uses | 2,6-Dimethyl-4-pyrone is used as a chemical and organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field. | | Reactions | 2,6-dimethyl-4H-pyran-4-one reacts with Phosgene at room temperature could yield 2,6-bis(4′-chloro-2′,6′-dimethylphenyl)-4H-pyran-4-one, and 2-(4′-chloro-2′,6′-dimethylphenyl)-6-methyl-4H-pyran-4-one[1].
 | | Synthesis Reference(s) | Journal of the American Chemical Society, 73, p. 300, 1951 DOI: 10.1021/ja01145a098 | | Synthesis | Step 1: (DADC) 2 mg of the complex (1 equiv) was dissolved in dry pyridine (20% solution) and cooled in an external ice/water bath under N2. The corresponding acid chloride 3 (4.4 equiv) was added at 0-5 C and stirred at room temperature for 1-2 days. After ice/HCl (2N) hydrolysis, the mixture was repeatedly extracted with CH2Cl2. The bound organic layer was washed with satd. NaHCO3 solution, dried (Na2SO4), decolorized (charcoal), filtered and concentrated. Conversion of 1.00 g 1 (2.34 mmol) with acetyl chloride according to method B and chromatographic purification gave 0.58 g (46%) of 4a.13C NMR (50 MHz, CDCl3):= 14.0 (q), 18.4 (q), 61.7 (t), 121.6, 164.0, 165.2, 171.7 ppm. Step 2: The diester was dissolved in a 5/1 mixture of 2N HCl and acetic acid (5%) and refluxed for 5-30 hours until TLC showed complete conversion. The reaction was hydrolyzed with satd. NaHCO3 solution and extracted with CH2Cl2. The bound organic layer was dried (Na2SO4), filtered and evaporated to give 5 without further purification. Colorless crystals of 2,6-dimethyl-4-pyrone 0.50 g (1.86 mmol) were obtained (87% yield). | | References | [1] Belsky, I. “The reaction of phosgene with 2,6-dimethyl-4H-pyran-4-one.” Tetrahedron 28 4 (1972): Pages 1001-1008.
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| | 2,6-Dimethyl-4H-pyran-4-one Preparation Products And Raw materials |
| Raw materials | heptane-2,4,6-trione-->2,2,6-Trimethyl-4H-1,3-dioxin-4-one-->Dehydroacetic acid-->Butanoic acid, 3-oxo-, 1-methylethenyl ester-->3,5-Diacetyl-2,6-dimethyl-4H-pyran-4-one-->3-Penten-2-one, 4-methoxy-, (3Z)--->diethyl 2,6-dimethyl-4-oxo-pyran-3,5-dicarboxylate-->N-(4-Methylphenyl)-3-oxobutanamide-->Dehydroacetic acid-->p-Toluidine | | Preparation Products | 2,6-Distyryl-4H-pyran-4-one |
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