3 Isobutylglutaric acid Spectral data

3-isobutylglutaric acid

3-(2-Methylpropyl)pentanedioic Acid;

Pentanedioic acid,3-(2-Methylpropyl)-

http://www.google.co.in/patents/WO1996038405A1?cl=en

Purified 3-isobutylglutaric acid is a solid with a melting point in the range of about 40°C to about 42°C.

¹H NMR (CDC1₃ 200 MHz) :

δ 0.92 (d, 6H, J = 6.6 Hz) ,

1.23 (dd, 2H, J_χ = 6.6 Hz, J₂ = 6.5 Hz) ,

1.64 ( , 1 H) ,

2.25-2.40 (m, 1 H) ,

2.40-2.55 (m, 4 H) .

¹³C NMR (CDCI₃) :

δ 22.4,

25.1,

29.5,

38.4,

43.4,

179.2, two carbonyls

IR (KBr) : 680.7, 906.4, 919.9, 1116.6, 1211.1, 1232.3, 1249.6, 1301.7,

1409.7, 1417.4, 1448.3, 1463.7, 1704.8, 2958.3, 3047.0 cm^"1.

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ARKIVOC 2010 (x) 266-275 

IR (cm-1): 3436, 2953, 1575;

1H NMR (D2O, δ ppm):

0.70 (d, 6H, CH3, J 6.0 Hz),
0.97 (s, 2H, CH2), 1.49 (s, 1H, CH), 1.95 (s, 4H, CH2), 2.05 (s, 1H, CH);

13C NMR (D2O, ppm):
182.89, 43.66, 31.90, 24.60, 22.27;

MS: m/z: 187 (M-H+);

Analysis calcd. for C9H16NO4:

C,57.43; H, 8.57% Found: C, 57.41; H, 8.55%.

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http://www.google.com/patents/US20070259917

Example 1

To a four neck round bottom flask fitted with a mechanical stirrer, condenser and charging tube, was charged isovaleraldehyde (1.0 kg, 11.61 mole), cyclohexane (1.35 L), ethyl cynoacetate (1.28 kg, 11.38 mole) and di-n-propylamine (11.74 g). The reaction mass was heated to reflux and water was removed azeotropically. After complete removal of water (˜208 ml), cyclohexane was distilled from the reaction mass followed by removal of traces of cyclohexane under vacuum. The reaction mass was cooled to 30-35° C. and diethyl malonate (2.027 kg, 12.67 mole) was added followed by addition of di-n-propylamine (106.91 g). The reaction mass was heated to 50-55° C. for 3-5 hours and then cooled to 25-30° C. Then hydrobromic acid (47%, 23.76 L) was added and the mass was refluxed at 100-125° C. for 6-10 hours. The reaction mass was cooled to 25-30° C. and extracted with toluene. The toluene was distilled off to obtain 3-isobutylglutaric acid in a yield of 1.54 kg (71%) having GC purity of 93.59%.

 NMR ASSIST

USE SPECTRUM OF GLUTARIC ACID TO UNDERSTAND ABOVE COMPD

GLUTARIC ACID

IR

1H NMR 

13 C NMR

2D [1H,1H]-TOCSY