Dodecylbenzene synthesis
- Product Name:Dodecylbenzene
- CAS Number:123-01-3
- Molecular formula:C18H30
- Molecular Weight:246.43
Yield:123-01-3 88%
Reaction Conditions:
Stage #1: n-Dodec-4-enwith Schwartz's reagent in tetrahydrofuran at 50; for 5 h;Inert atmosphere;Sealed tube;
Stage #2: iodobenzenewith 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide;triphenylphosphine in tetrahydrofuran at 20; for 24 h;Inert atmosphere;Irradiation;Sealed tube;
Steps:
14. Chain walking and cross-coupling
General procedure: General procedure JIn an argon-filled glovebox, a flame-dried 10 mL sealing tube equipped with a Teflon septumand magnetic stir bar was charged with ZrCp2HCl (258 mg, 1.0 mmol, 2.0 equiv.), the reactionvial was sealed tightly and removed from the glovebox, anhydrous THF and alkene (1.1 mmol,2.2 equiv.) were added by a syringe under an argon atmosphere. The mixture was stirred at 50oC for a specific time until a clear yellow solution was obtained.In an argon-filled glovebox, another flame-dried 10 mL sealing tube equipped with a Teflonseptum and magnetic stir bar was charged with corresponding organic halide (0.5 mmol, 1.0equiv.), Ni cat. (1 mol%), tetrabutylammonium 4-toluenesulfonate (207 mg, 0.5 mmol, 1.0equiv.), the reaction vial was sealed tightly and removed from the glovebox, the previous clearalkyl zirconium reagent was transferred via syringe over 1 min to this reaction vial under anargon atmosphere. The reaction mixture was then stirred and irradiated with blue LEDs with afan placed above for cooling. After 24 h, the reaction mixture was diluted with CH2Cl2, filteredthrough a short pat of silica gel, and concentrated in vacuum. Purification of the crude productby flash chromatography on silica gel afforded the desired product.
References:
Bai, Songlin;Gao, Yadong;Jiang, Chao;Liu, Xiaolei;Qi, Xiangbing;Wang, Jing;Wu, Qingcui;Yang, Chao [Chem,2020,vol. 6,# 3,p. 675 - 688] Location in patent:supporting information
112-80-1
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123-01-3
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