Hexanoic acid, 3-cyano-5-methyl-, ethyl ester synthesis

12synthesis methods

Product Name:Hexanoic acid, 3-cyano-5-methyl-, ethyl ester
CAS Number:181289-17-8
Molecular formula:C10H17NO2
Molecular Weight:183.25

186038-82-4 Synthesis

186038-82-4
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Hexanoic acid, 3-cyano-5-methyl-, ethyl ester

181289-17-8
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Yield:181289-17-8 94%

Reaction Conditions:

with water;sodium chloride in dimethyl sulfoxide at 25 - 145; for 10 - 12 h;

Steps:

3

Example-3:; Preparation of 3-Cyano-S-methyl-hexanoic acid ethyl ester; PG-03100 g of 2-carbethoxy-3-cyano-5-methyl hexanoic acid ethyl ester above and 27.0 g of sodium chloride IP were treated with 270 niL DMSO and 13.6 mL of R.O. water at 25°C to 35⁰C. The reaction mixture was slowly heated to get 14O⁰C to 145⁰C temperature within 1-2 hour. The reaction mixture was stirred for 9-10 hours and gradually cooled to 25⁰C to 35⁰C. 210 mL of methyl tert-butyl ether was added to the reaction mixture followed by addition of 180 mL of water is slowly added in 1-2 hour below 35⁰C, stirred and settled for 30 minutes. The separated aqueous layer was treated with 210 mL methyl tert-butyl ether, stirred and settled for 30 minutes. The separated organic layer was combined and treated with 200 mL of water, stirred and settled for 30 minutes. The separated organic layer was distilled under vacuum below 6O⁰C to remove excess methyl tert-butyl ether. [% Yield = 94%, G.C purity = 94-96%] IR (Nujol-mull, v cm⁴) : sp³ C-H stretch : 2960, 2935, 2902; CN : 2243, CO : 1739. ¹H NMR (CDCl₃, 300 MHz): δ 0.89-0.98 (m, 6H), 1.19-1.36 (m, 4H), 1.61-1.64 (m, IH), 3.30-3.33 (m, IH), 2.50-2.57 (dd, IH, J = 7.78 Hz, J = 17.94 Hz), 2.65-2.73 (dd , IH, J = 7.8 Hz, J = 17.8 Hz), 3.03-3.21 (m, IH), 4.16-4.23 (q, 2H, J - 7.13 Hz). MS: m/z = 184.2 (M+l).3-Cyano-S-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 mm Film thickness : 5 μm Injector Temperature : 21O⁰CDetector Temperature : 23O⁰COven temperature Time (min) TemperatureInitial 0 100⁰C Final 44 22O⁰CTemp Programme rate: 20°C/minuteEqulibrium time : 1.0 minuteInjection Volume : 0.5 μlCarrier gas : Nitrogen Split Flow : 60 ml/min.Detector : FIDA sample Chromatogram is shown in Figure- VII