ChemicalBook CAS DataBase List ALLYL CAPRYLATE

ALLYL CAPRYLATE synthesis

6synthesis methods

Product Name:ALLYL CAPRYLATE
CAS Number:4230-97-1
Molecular formula:C11H20O2
Molecular Weight:184.28

By esterification of caprylic acid with allyl alcohol in benzene in the presence of naphthalene-β-sulfonic acid.

5831-77-6 Synthesis

5831-77-6
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124-07-2 Synthesis

124-07-2
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4230-97-1
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Yield: 98%

Reaction Conditions:

Stage #1:2-allyloxypyridine;Octanoic acid with methyl trifluoromethanesulfonate in toluene at 0 - 23; for 1 h;Inert atmosphere;
Stage #2: with potassium carbonate in toluene for 2 h;Reflux;Inert atmosphere;

Steps:

General Procedure for the formation of allyl esters
General procedure: A 5-mL reaction vial was equipped with a stir bar, a rubber septum, and an argon inlet needle. The vial was charged with allyloxypyridine (2) (1.1 equiv), carboxylic acid (4) (1.0 equiv), and dry PhCH3 (2.5 mL), and was allowed to stir at 0 °C. MeOTf (1.1 equiv) was added dropwise to the reaction mixture over 2min. Upon complete addition, the ice bath was removed and the reaction was allowed to stir for 1h or until 2 was completely consumed as indicated by TLC. The septum was quickly replaced with a reflux condenser fitted with an N2 inlet adapter. The reaction mixture was heated at reflux (oil bath 115 °C), and K2CO3 (0.95 equiv) was added in one portion through the top of the reflux condenser. Upon complete consumption of the carboxylic acid as indicated by TLC (typically 1-2 h), the mixture was diluted with ethyl acetate (10 mL). The diluted reaction mixture was washed with water (10 mL), followed by brine (10 mL). The organic fraction was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to isolate the crude product mixture. The crude mixture was purified by flash chromatography to yield the allyl ester product (5).

References:

Strayer, Timothy A.;Culy, Caleb C.;Bunner, Matthew H.;Frank, Amie R.;Albiniak, Philip A. [Tetrahedron Letters,2015,vol. 56,# 48,p. 6807 - 6809] Location in patent:supporting information