ChemicalBook CAS DataBase List DIETHYL (1-CYANO-3-METHYLBUTYL)MALONATE

DIETHYL (1-CYANO-3-METHYLBUTYL)MALONATE synthesis

6synthesis methods

Product Name:DIETHYL (1-CYANO-3-METHYLBUTYL)MALONATE
CAS Number:186038-82-4
Molecular formula:C13H21NO4
Molecular Weight:255.31

diethyl 2-(3-methylbutylidene)propanedioate

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143-33-9 Synthesis

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Yield: 97.97%

Reaction Conditions:

in ethanol at 25 - 35; for 2 - 3 h;

Steps:

2
Example-2:; Preparation of 2-carbethoxy-3-cyano-5-methyl hexanoic acid ethyl ester; PG-02 100.0 g of 2-carbethoxy-5-methyl hex-2-enoic acid ethyl ester prepared above was added slowly to the solution of 21.0 g of sodium cyanide in 100 niL of ethanol over a period of 2-3 hours at 25⁰C to 35⁰C. 91.0 mL of hexane was added at 25⁰C to 35⁰C and 27.0 mL of acetic acid was added in 30 minutes which resulted in thick slurry. 81.8 mL of water was added to the reaction mixture and was stirred and settled for 30 minutes resulted in a clear solution. Separated aqueous layer was treated with 91.0 mL of hexane, stirred and settled for 15 minutes at 25⁰C to 35⁰C. Separated organic layer were combined and treated with 91.2 mL of water. The Separated hexane layer was filtered through hyflowbed and washed with hexane. The filtrate was subjected to distillation under vacuum by hot water below 6O⁰C to remove excess of hexane, cooled to 25⁰C to 35⁰C. [% Yield = 97.97%; GC purity = 92-95%]. IR (Nujol-mull, v Cm^"1) : sp³ C-H stretch : 2981, 2962, 2937; CN : 2245, CO : 1755, 1739. ¹H NMR (CDCl₃, 300 MHz): δ 0.96-0.99 (t, 6H, J = 4.5 Hz), 1.20-1.29 (m, 6H), 1.30- 1.33 (m, IH), 1.60-1.68 (m, 2H), 3.30-3.33 (m, IH), 3.53-3.56 (d, IH, J = 8.19 Hz), 4.22-4.32 (m, 4H). MS: m/z = 256.31 (M+l).2-carbethoxy-3-cyano-5-methyl hexanoic acid ethyl ester purity may be determined by using the following gas chromatography apparatus and procedures:Column & Packing : Fused silica capillary column Elite-5 of Perkin Elmer or equivalent Length : 30 m Diameter : 0.53 mmFilm thickness : 5 μm Injector Temperature : 21O⁰C Detector Temperature : 23O⁰COven temperature Time (min) Temperature Initial 0 100⁰CFinal 44 22O⁰CTemp Programme rate: 20°C/minute Equlibrium time : 1.0 minuteInjection Volume : 0.5 /^l Carrier gas : NitrogenSplit Flow : 60 ml/minDetector : FIDA sample Chromatogram is shown in Figure- VI