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ChemicalBook CAS DataBase List CROTONIC ACID ISOPROPYL ESTER
6284-46-4

CROTONIC ACID ISOPROPYL ESTER synthesis

3synthesis methods
-

Yield:6284-46-4 77%

Reaction Conditions:

with sulfuric acidReflux;

Steps:

Preparation of isopropyl but-2-E-enoate (22)

Was prepared from crotonic acid 20 (872 mmol, 75 g), isopropanol (365 mL) and concentrated sulfuric acid (8.8 mL) according to the previous procedure, work-up and isolation, to afford ester 22 (86.5 g ca. 77%) as a colourless oil which was used in the next step without purification. The following data were obtained from a small purified sample (flash chromatography, 10% diethyl ether in hexane): Rf (20% diethylether in hexane) 0.59; δH (400 MHz, CDCl3) 7.00-6.89 (m, 1H), 5.82 (d, J = 15.7, 1H), 5.10-5.02 (m incl. app. septet, J = 6.3, 1H), 1.86 (d, J = 6.3, 3H), 1.25 (d, J = 6.3, 6H); δC(100 MHz, CDCl3) 166.1, 144.0, 123.3, 67.3, 21.9, 17.8; max(film)/cm-1 3539, 3422, 2981, 2878, 1720, 1660, 1446, 1375, 1293, 1191, 1110, 1002, 834, 690; HRMS (EI+, [M]+) calcd. for C7H12O2 128.0832, found 128.0830. The data were in agreement with those reported by Jonczyk et al. [S2].

References:

Laurenson, James A. B.;Parkinson, John A.;Percy, Jonathan M.;Rinaudo, Giuseppe;Roig, Ricard [Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 2660 - 2668] Location in patent:supporting information