Organic residuals from water supplies

High-Performance Concentration System for the Isolation of Organic Residues from Water Supplies... 

Water Treatmeat and Supply. Before water is consumed, it has to be collected first from either underground or above-ground sources. Therefore, source control is one of the most important tasks of water supply. Except for a few municipalities where the source water derived from deep aquifers, source water has to be treated to remove contaminants such as pathogenic bacteria, heavy metals, and pesticide residues. The process of treatment involves the removal of suspended solids and the use of chemicals or ultraviolet (UV) radiation to disinfect unwanted organisms so that the effluent water satisfies quality requirements dictated by the Federal Safe Drinking Water Act. For water used by industrial plants such as paper mills or nuclear power plants, special treatment is needed and its discharge is regulated. 

The product from Step 2 (2.06 mmol) was dissolved in 10 ml THE and added drop wise to a stirred suspension of NaH (2.27 mmol) in 5 ml THE at ambient temperature. After 15 minutes, the product from Step 1 (2.1 mmol) dissolved in 5 ml THE was added, the mixture stirred for several hours and was then quenched with 1 ml water. The organic phase was evaporated and the residue purified by column chromatography on silica with CH2Cl2/methyl alcohol, 95 5, yielding a Z/E geometric isomer ratio of 76 24, respectively. The desired Z-isomer was isolated by re-crystallization, mp = 189-190 °C. H-NMR and mass spectrum data supplied. 

The product from Step 1 (13.4 mmol) was dissolved in 100 ml apiece THE and a saturated solution of NH4CI, placed in a water bath, and activated zinc dust (230 mmol) added. The mixture stirred 20 minutes and was then filtered through a pad of diatomaceous earth. The organic layer was separated and the aqueous layer extracted with 20 ml THF. The organic phase was washed with brine, dried, and concentrated. The residue was triturated with 20 ml water and the product isolated in 71% yield as a tan solid. NMR data supplied. 

The product from Step 1 (6.25 mmol) was dissolved in 32 ml ethylene glycol dimethylether, cooled to -10°C, POCI3 (16.3mmol) added followed by the dropwise addition of triethylamine (32.6 mmol) dissolved in 3 ml ethylene glycol dimethylether, and the reaction temperature kept below —5°C. The mixture was gradually warmed to ambient temperature over 1 hour, quenched with water, and extracted with EtOAc. The organic phase was washed with saturated aqueous NaHCOj, dried, and concentrated. The residue was triturated with petroleum ether, filtered, and the product isolated in 90% yield. NMR data supplied. 

The product from Step 5 (11 mmol) was dissolved in 10 ml N,N-dimethylformamide, the product from Step 2 (7.7 mmol) and K2CO3 (8.8 mmol) added, and the mixture stirred at ambient temperature for 16 hours. The solvent was removed and the residue partitioned between EtOAc and water. The organic phase was separated, washed, dried, concentrated, purified by flash chromatography on silica gel using 0-4% methyl alcohol/CH2Cl2, and the product isolated as a yellow solid. MS data supplied. 

O-Methylhydroxylamine hydrochloride (0.4mol) and lOg 3A molecular sieves were added to a solution of the product from Step 1 (0.1 mol) dissolved in 50 ml methyl alcohol and the mixture stood at ambient temperature 16 hours. The solution was concentrated, the residue partitioned between methyl t-butyl ether and water, the organic phase washed, dried, concentrated and the product isolated in 100% yield as 1 1 E/Z isomer mixture. H-NMR data supplied. (Note 3)... 

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