ChemicalBook CAS DataBase List (2Z)-3,7-Dimethyl-2,6-octadienoic acid

(2Z)-3,7-Dimethyl-2,6-octadienoic acid synthesis

12synthesis methods

Product Name:(2Z)-3,7-Dimethyl-2,6-octadienoic acid
CAS Number:4613-38-1
Molecular formula:C10H16O2
Molecular Weight:168.23

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4613-38-1
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Yield: 87%

Reaction Conditions:

with sodium chlorite;sodium dihydrogenphosphate;2-methyl-but-2-ene in water;acetone at 20; for 4 h;

Steps:

1.2.2. The synthesis of (E)- and (Z)-3,7-dimethylocta-2,6-dienoic acid
A solution of 30.95 g (342 mmol) of NaClO2 and 49.8 g (319 mmol) of NaH2PO4 in 286 mL distilled water was added dropwise to a stirred mixture of 5.74 g (37.8 mmol) of Z-geranial and 59.4 mL 2-methylbut-2-ene in 236 mL of acetone in a1000 mL round flask over 4 h at ambient temperature. The mixture was stirred for another 1 h at ambient temperature. After the reaction was finished as detected by TLC, the reaction mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude residue was purified by silicagel chromatography and eluted with PE/ EtOAc to give Z-geranic acid (5.52 g, 87%) as a colorless oil. 1H NMR ( 300 MHz,CDCl3 ) δ: 12.01 (br, 1H ), 5.68 (d, J = 0.8 Hz, 1H ), 5.17-5.11 (m, 1H ), 2.64 (t, J = 7.5 Hz, 2H), 2.20-2.12 (m, 2H), 1.93 (s,3H), 1.69 (s, 3H ), 1.62 (s, 3H ). In a same protocol, E-geranic acid was prepared as a colorless oil in 91% yield. 1H NMR(300 MHz, CDCl3) δ: 12.05 (br, 1H), 5.69 (br, 1H), 5.07 (br, 1H), 2.20-2.15 (m, 7H), 1.69 (s, 3H), 1.61 (s, 3H). These datawere consistent with that in references.

References:

Wang, Weiwei;Zhang, Xiaoteng;Zhao, Yu;Liu, Xinlei;Zhang, Zhenhua;Wang, Mingan [Chinese Chemical Letters,2018] Location in patent:supporting information

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