| Identification | Back Directory | [Name]
2-METHOXY-5-PICOLINE | [CAS]
13472-56-5 | [Synonyms]
2-METHOXY-5-PICOLINE
2-Methoxy-5-methylpyridine
Pyridine,2-Methoxy-5-Methyl- | [Molecular Formula]
C7H9NO | [MDL Number]
MFCD08703669 | [MOL File]
13472-56-5.mol | [Molecular Weight]
123.152 |
| Chemical Properties | Back Directory | [Appearance]
colorless liquid | [Boiling point ]
165°C(lit.) | [density ]
1.001±0.06 g/cm3(Predicted) | [refractive index ]
1.5000 to 1.5040 | [storage temp. ]
Room temperature. | [form ]
clear liquid | [pka]
3.69±0.10(Predicted) | [color ]
Colorless to Light yellow | [λmax]
279nm(CH3CN)(lit.) |
| Hazard Information | Back Directory | [Chemical Properties]
colorless liquid | [Synthesis]
Example 5: General procedure for the preparation of 2-methoxy-5-methylpyridine from 2-bromo-5-methylpyridine
1. 250 g (1.45 mol) of 2-bromo-5-methylpyridine, 2.1 g (1 mol%) of copper(I) bromide (CuBr), 14.5 g (2 mol%) of poly(ethylene glycol) dimethyl ether 500, and 457 g of 30% sodium methanol solution (precursor concentration of 14.5%) were added to a reactor.
2. the reaction mixture was heated to 90 °C and the progress of the reaction was monitored by GC until the conversion was >98.5% (reaction time totaled 17 hours).
3. upon completion of the reaction, the reaction mixture was quenched by slowly adding 750 g of water.
4. The pH of the mixture was adjusted to 9 by dropwise addition of hydrochloric acid, followed by filtration through decalite to remove insoluble material.
5. The aqueous phase was extracted twice with methyl tert-butyl ether (MTBE) (350 g each).
6. The organic phases were combined and subjected to vacuum fractionation to afford 162.8 g (1.32 mol, 91% yield) of 2-methoxy-5-methylpyridine with a GC purity of >98% (a/a). | [References]
[1] Patent: US2008/71084, 2008, A1. Location in patent: Page/Page column 4 |
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