- Synthetic Approach of Dimethyl decanedioate
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Dimethyl dioate (CAS NO.: ), which is also known as Decanedioic acid, di, could be produced through the following synthetic routes.
The electrode assembly is constructed; the platinum electrodes are positioned vertically, parallel, and about 5 mm apart by careful bending of the lower platinum wire connections.
To a 500-mL, round-bottomed flask having a central 34/45 standard taper neck and two 24/40 standard taper necks are added 120 g (0.75 mol) of methyl hydrogen hexanedioate, 250 mL of methanol, 4.1 g (0.075 mol) of sodium methoxide, 10 mL of pyridine, and a magnetic stirring bar. The electrode assembly is inserted so that the platinum electrodes are immersed in the solution. A thermometer and reflux water condenser are attached. The mixture is heated to 60°C and stirred until the sodium methoxide dissolves.
The mixture is electrolyzed with a constant current of 1.1 A until GLC analysis of the solution shows the absence of the peak due to methyl hydrogen hexanedioate. This requires about 23 hr; electrolysis is continued for an additional 2.5 hr at the same current. Throughout the electrolysis the reaction mixture is maintained at 62–65°C by passage of the current. After about 1 hr of electrolysis, when conditions are stabilized, the reaction may be left unattended.
The yellow reaction mixture is allowed to cool and then is acidified with 20 mL of glacial acetic acid. The acidified solution is transferred with methanol washing to a 1-L round-bottomed flask and evaporated (70–80°C, 12 mm) to dryness. The solid residue is stirred with 500 mL of diethyl ether for 1 hr. Undissolved solids are removed by filtration and the residue is washed twice with 100-mL portions of diethyl ether. The combined filtrate and washings are washed with aqueous sodium carbonate until neutral and then three times with 200-mL portions of water. The ether solution is dried over anhydrous calcium sulfate. Filtration and evaporation of the ether afford a yellow oil that is distilled under reduced pressure through a Vigreux column (30 × 2.5 cm). This gives 6–7 g of dimethyl hexanedioate (bp 69–71°C, 0.02 mm), 3–4 g of a mixed fraction (bp 72–105°C, 0.02 mm), and 60–61 g (70–71%) of dimethyl decanedioate (bp 105–107°C, 0.02 mm). The dimethyl decanedioate crystallizes on standing at room temperature, mp 26.5–27.2°C.
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