- One Synthetic Approach of t-Butyl cyanoacetate
-
t- (CAS NO.: ), which is also known as , tert-butyl ester, could be produced through the following synthetic routes.
In a 5-l., three-necked, round-bottomed flask equipped with a rubber- or mercury-sealed mechanical stirrer and a reflux condenser carrying a drying tube are placed 340 g. (4 moles) of cyanoacetic acid and 2 l. of anhydrous ether. To the stirred solution, 834 g. (4 moles) of phosphorus pentachloride is added in portions through the third neck of the flask, which is sealed between additions. The mixture is cooled occasionally with an ice bath to prevent excessive refluxing, and, after the addition is complete, stirring is continued for 0.5 hour or until the phosphorus pentachloride dissolves completely. The reflux condenser is removed and replaced with apparatus for downward distillation, and the ether is distilled from a water bath at 50–60°, after which most of the phosphorus oxychloride is removed at reduced pressure (20–25 mm. with a bath temperature of 55–65°), the receiver being cooled in an ice-salt bath. The red, oily residue is dissolved in 200 ml. of benzene and the benzene and residual phosphorus oxychloride distilled under reduced pressure. This operation is repeated with 200 ml. of fresh benzene to ensure complete removal of phosphorus oxychloride. The residue is then cooled to room temperature and is transferred to a 500-ml. pressure-equalized dropping funnel for immediate use in the following step.
The same 5-l. flask used in the preceding step is used again, without washing; it is fitted with a reflux condenser carrying a drying tube, a sealed mechanical stirrer, and the dropping funnel containing the acid chloride. In the flask are placed 296 g. (4 moles) of dry t-butyl alcohol and 484 g. (4 moles) of dimethylaniline in 600 ml. of anhydrous ether. The acid chloride is added dropwise to the stirred solution, the mixture being cooled occasionally with an ice bath to prevent excessive refluxing. After the addition is complete, the reaction mixture is refluxed for 2 hours and then stirred gently at room temperature for 15 hours. Two liters of water is added with stirring, and the mixture is filtered with suction through a Büchner funnel fitted with a matting of glass wool. The matting is washed with three 250-ml. portions of ether. After separation of the combined ethereal layers, the aqueous layer is extracted twice with 250-ml. portions of ether. The combined ether solutions are washed with successive portions of 2N sulfuric acid (a total of 1 l.) until free of dimethylaniline, then with two 200-ml. portions of 2N sodium carbonate solution, and dried over sodium carbonate. After removal of the ether by distillation, the residue is transferred to an alkali-washed flask and distilled at reduced pressure through a 20-cm. alkali-washed Vigreux column. The yield of colorless product is 355–378 g. (63–67%) boiling at 67–68°/1.5mm. (90°/10 mm., 54–56°/0.3 mm), nD20 = 1.4198.
Prev:No record
Next:No record - 【Back】【Close 】【Print】【Add to favorite 】
- Related information
- Production Method of DI-t-Butyl nitroxide
- Preparation of Phenyl t-Butyl ether
- One Synthetic Approach of Ethyl (1-phenylethylidene)cyanoacetate
- Synthesis of Ethyl cyanoacetate
- One Synthetic Approach of Glycine t-Butyl ester
- Preparation of Di-tert-butyl malonate
- Synthesis of t-Butyl azidoformate
- Production Method of t-Butyl azodiformate
- Production Method of t-butyl carbazate
- Preparation of t-Butyl diazoacetate
-
Health and Chemical more >
-
Hot Products
- 67514-60-7 Propane, 1,2-dichloro-1-ethoxy-
- 126534-31-4 (S)-2-CHLORO-1-(2,4-DICHLOROPHENYL)ETHANOL
- 116-02-9 3,3,5-Trimethylcyclohexanol
- 7782-82-3 SODIUM HYDROGEN SELENITE
- 17689-77-9 (Triacetoxy)ethylsilane
- 24938-64-5 POLY-p-PHENYLENE TEREPHTHALAMIDE
- 99899-09-9 Phenol, 2-[1-[[2-[(2-hydroxyethyl)amino]ethyl]imino]ethyl]-
- 68513-65-5 Butane, branched and linear
- 138-52-3 2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside
- 7299-42-5 alpha,alpha-Dimethyl-4-methylenecyclohexanemethanol
- 31138-65-5 Sodium glucoheptonate
- 906673-24-3 5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole