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20-(Benzyloxy)-20-oxoicosanoic acid synthesis

4synthesis methods
-

Yield:1334703-62-6 43%

Reaction Conditions:

with toluene-4-sulfonic acid in toluene at 40;Dean-Stark;Reflux;

Steps:

5 Example 5: 20-(Benzyloxy)-20-oxoicosanoic acid

In a reactor equipped with a Dean Stark trap,50 g of eicosanedioic acid, 1.2 g of p-toluenesulfonic acid (pTSA), 500 g of toluene and 9.5 g of benzyl alcohol were charged.The mixture was refluxed until no more water was collected from the Dean Stark separator. The reaction was cooled to 40 ° C and filtered.The filter cake (unreacted starting material) was combined with 0.6 g of p-toluenesulfonic acid, 250 g of toluene and 6.3 g of benzyl alcohol.And put it back into the reactor equipped with the Dean Stark separator.The reaction was cooled to 45 ° C and filtered. The filter cake (10 g unreacted raw material) was dried and set aside.Can be used in the next batch. The mother liquid of the solid-liquid separation was cooled to 12 ° C, and the precipitated product was separated by filtration.The filter cake was recrystallized from 200 g of 2-propanol.27 g of the title compound were obtained.GC-MS analysis of the product sample (derivatized with BSTFA) showed that the product contained 99.5% of the title compound,0.2% eicosanedioic acid and a small amount of other impurities (mainly homologues of the product).

References:

CN108314621,2018,A Location in patent:Paragraph 0068; 0069; 0070; 0078