Pyridine-2,6-dimethanol

Trimethoxybenzoic acid Thionyl chloride Pyridine-2,6-dimethanol... 

A solution comprising 3,24 kg (23.3 mols) of pyridine-2,6-dimethanol in 35 liters of pure pyridine was added to the residue and the mass was heated to 80°C for 2 /a hours. The reaction mass became brown in color. The chlorhydrate of pyridine so formed was cooled and crystallized. The resulting reaction mass was then poured into water. The precipitate obtained was filtered, repeatedly rinsed with water, and dissolved in 400 liters of methanol. The resulting solution was filtered with activated charcoal. From this filtration 50 liters of methanol were distilled at normal pressure and then crystallized. 8.35 kg (15.8 mols) of pyridine-2,6-dimethanol trimethoxybenzoate were obtained, which represented a yield of 68%. 

In 1975, Weber and Vogtle showed that open-chained polyethers, 2,6-pyridine-dimethanol, and ortho-xylene derivatives terminated in an 8-quinolinyl group could form stable, 1 1, crystalline complexes with a variety of metal salts. The podands were prepared from 8-hydroxyquinoline and the corresponding dihalides. A typical example is shown in Eq. (7.10). 

CniHifiN205 138681-67-1) see Zafirlukast a -(nitromethyl)-3-(phenylmethoxy)-2,6-pyridine-dimethanol... 

Synthesis of the bis-p-nitrophenylcarbonate of 1,4-benzene-dimethanol A solution of 14.1 g (70 mmoles) of p-nitrophenylchloroformate in 40 mL of dry dichloromethane is added over a period of one hour to a solution of 4.80 g (35 mmoles) of 1,4-benzenedimethanol in 5.53 g (70 mmoles) of dry pyridine and 60 mL of dry dichloromethane. After stirring at room temperature overnight, enough dichloromethane is added to the reaction mixture to bring the white compound formed into solution. The organic phase is then washed successively with... 

Ethyl 3-chloro-3-oxopropanoate (ethyl malonyl chloride, 2.3 mL, 18.09 mmol) was added to a stirred solution of benzene-1,2-dimethanol (1.00 g, 7.24 mmol) and pyridine (1.5 mL, 18.09 mmol) in CH2CI2 (100 mL) at 0°C. The solution was allowed to slowly... 

Cyclohexanedimethanol monoacetate. A mixture of cis tmd trans 1,4-cyclohexane dimethanol, (930 g, 6.448 moles) wtis dissolved in 3 L of tetrahydrofuran and 550 mL of pyridine, (7.69 moles) added. The solution was cooled in an ice bath and stirred under argon. An acetyl chloride solution, (506.4 g, 6.45 moles) in 500 mL of tetrahydrofuran was added dropwase over a 2 hour period. The ice bath was removed and the reaction mixture stirred for 2 hours at room temperature. It was then filtered to remove the pyridine HCl salt and evaporated to remove the tetrahydrofuran. The residue was dissolved in 2 L of ethyl acetate and the solution extracted with diluted aqueous HCl (2 x 300 mL), warm water (2 x 300 mL) and aqueous NaHC03 solution (2 X 300 mL). The ethyl acetate solution was dried over anhydrous MgS04 and the ethyl acetate removed on a rotoevaporator. Vacuum distillation of the residue yielded 335 g of product. GC analysis showed that the product contained 59% cyclohexanedimethanol monoacetate and 41% cyclohexanedimethanol diacetate. The overall yield of the monoacetate was 16.5%. 

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