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ChemicalBook CAS DataBase List CETYL PALMITATE
540-10-3

CETYL PALMITATE synthesis

12synthesis methods
1-Hexadecanol

36653-82-4

CETYL PALMITATE

540-10-3

GENERAL METHOD: 1.0 g (7.69 mmol) of 1-hexadecanol was added to a 50 mL round-bottomed flask, followed by 0.523 g (0.66 eq.) of NaBr and 0.383 g (0.33 eq.) of NaBrO3, and 10 mL of H2O [this aqueous solution has a molar ratio of bromide to bromate of 2:1]. The reaction mixture was stirred vigorously to ensure complete dissolution of the contents. An aqueous solution of H2SO4 (0.5 equiv, prepared from 0.21 mL of 98% H2SO4 with 1 mL of water) was slowly added to the above reaction mixture at room temperature with continuous stirring for 2.5 hours. The reaction mixture was continued to be stirred for up to 24 hours. Upon completion of the reaction, the product was extracted with CH2Cl2 (3 x 15 mL) and the organic layer was dried with Na2SO4, followed by removal of the solvent to afford hexadecanoic acid hexadecyl ester in 98% yield (0.953 g) as a colorless liquid. The structure of the product was confirmed by GC-MS and NMR.

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Yield:540-10-3 99%

Reaction Conditions:

with sodium bromate;sulfuric acid;sodium bromide in water at 20; for 24 h;

Steps:

General procedure for octyl octanoate (2a)
General procedure: A total of 1.0 g of 1-octanol (7.69 mmol) was taken in a 50-mL round-bottomed flask, to it NaBr 0.523 g (0.66 eq.), NaBrO 3 0.383 g (0.33 eq.), and 10 mL of H 2 O [comprises the bromide and bromate in 2:1 molar ratio] were added[6f]. The reaction mixture was stirred vigorously to dissolve the contents completely. To the above reaction mixture, the aqueous H 2 SO 4 solution (0.5 eq.) was added slowly under stirring over a period of 2.5 h at room temperature (prepared by adding 0.21 mL of 98% H 2 SO 4 to 1 mL of water). The reaction mixture was allowed to stir for up to 24 h. After the completion of reaction, the product was extracted with CH 2 Cl 2 (3 15 mL), the organic layer was dried with Na 2 SO 4 and removal of the solvent obtained octyloctanoate in 98% yield (0.953 g) as colorless liquid. The product was confirmed by GC-MS as well as by NMR.

References:

Reddy, N. Naresh Kumar;Ravi, Chitrakar;Adimurthy, Subbarayappa [Synthetic Communications,2018,vol. 48,# 13,p. 1663 - 1670]

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