ChemicalBook CAS DataBase List 2,2-dimethylbut-3-enoic acid

2,2-dimethylbut-3-enoic acid synthesis

13synthesis methods

Product Name:2,2-dimethylbut-3-enoic acid
CAS Number:10276-09-2
Molecular formula:C6H10O2
Molecular Weight:114.14

3-Butenoic acid, 2,2-diMethyl-, Methyl ester

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Yield:10276-09-2 88%

Reaction Conditions:

with hydrogenchloride

Steps:

3 2,2-Dimethyl-but-3-enoic acid
2,2-Dimethyl-but-3-enoic acid The above ethereal solution of 2,2-dimethyl-but-3-enoic acid methyl ester (10 g) was diluted with ethanol (25 ml), sodium hydroxide (4 M, 22 ml) was added and the mixture was stirred overnight. The solution was partially evaporated to remove the ethanol and the resultant mixture was added to HCl (1M, 100 ml). The product was extracted with ethyl acetate and the extracts were dried and evaporated to give 2,2-dimethyl-but-3-enoic acid (6.01 g, 88% 2 steps). (Hayashi et al., J. Org. Chem., 65:8402-8405 (2000). ¹H NMR (400 MHz, CDCl₃) δ 1.33 (s, 6H); 5.11 (d, J=10.8 Hz, 1H, -CH=CH₂); 5.15 (d, J=17.2 Hz, 1H, -CH=CH₂); 6.05 (dd, J=17.2, 10.8 Hz, 1H, -CH=CH₂).

References:

Palladino, Michael A.;Lloyd, George Kenneth;Hayashi, Yoshio;Nicholson, Benjamin US2005/197344, 2005, A1

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