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ChemicalBook CAS DataBase List 1-Bromohexadecane
112-82-3

1-Bromohexadecane synthesis

7synthesis methods
Synthesis of 1-Bromohexadecane from hexadecanol by bromination: put hexadecanol into the reaction pot and stir, heat, melt and put in red phosphorus. Add bromine drop by drop at 100℃ with sufficient stirring on one side, control 120-130℃, about 6h drop by drop, continue the reaction and drain the hydrogen bromide. Cool to below 50 ℃, add saturated and sodium chloride, stirring and washing, resting stratification, parting off the lower waste stream, then wash with water to neutral, distillation, collect 220-230 ℃ (2kPa) fraction, to obtain 1-bromohexadecane.
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Yield:112-82-3 99%

Reaction Conditions:

with ethyl 2,2-dibromoacetoacetate;triphenylphosphine in dichloromethane at 20; for 0.25 h;

Steps:

General Procedure for the Synthesis of products

General procedure: Ethyl α,α-dibromoacetoacetate 2a (0.41 mmol, 1.2 equiv), alcohols 1a-1s (0.34 mmol, 1.0 equiv) and Ph3P (0.68 mmol, 2.0 equiv) were added under ambient temperature to 3 mL of DCE in air. After stirred at room temperature for appropriate time (monitored by TLC), the reaction was quenched by addition of H2O (3 mL) and then extracted with ethyl acetate (3×3 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silica gel with petroleum ether or mixture of petroleum ether and ethyl acetate as eluent to afford the corresponding products 3a-3s.

References:

Cui, Xiao-Meng;Guan, Yong-Hong;Li, Na;Lv, Hao;Fu, Lin-An;Guo, Kun;Fan, Xiaohui [Tetrahedron Letters,2014,vol. 55,# 1,p. 90 - 93] Location in patent:supporting information

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