1,1-Dichloro-4-methylpenta-1,3-diene synthesis
- Product Name:1,1-Dichloro-4-methylpenta-1,3-diene
- CAS Number:55667-43-1
- Molecular formula:C6H8Cl2
- Molecular Weight:151.03
62434-98-4
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Yield:55667-43-1 94%
Reaction Conditions:
with toluene-4-sulfonic acid at 130; for 2 h;
Steps:
To pure 1,1-dichloro-4 methyl-1,4-diene (59.0 g, 391 mmol, 1 equiv.) was added PTSA (550 mg, 2.6 mmol, 0.006 equiv.) and the mixture was heated at 130°C during 2 h.The cooled residue was distilled under reduced pressure (P = 13 mmHg, bp = 62-65°C) toyield conjugated 1,1-dichloro-4 methyl-1,3-diene (55.3 g, 366 mmol, 94%) as a colorless oil. 1H NMR (300 MHz, CDCl3): = 6.58 (d, J = 10.8 Hz, 1H), 5.95 (dh, J = 10.8, 1.4 Hz, 1H,),1.83 (s, 3H), 1.76 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3): = 140.2, 125.6, 119.7, 119.0, 26.4, 19.1 ppm.
References:
Fenneteau, Johan;Vallerotto, Sara;Ferrié, Laurent;Figadère, Bruno [Tetrahedron Letters,2015,vol. 56,# 24,p. 3758 - 3761] Location in patent:supporting information
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