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ChemicalBook CAS DataBase List Benzyl benzoate
120-51-4

Benzyl benzoate synthesis

15synthesis methods
By the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by reaction of sodium benzylate on benzaldehyde.
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Yield:120-51-4 100%

Reaction Conditions:

with triethylamine at 90; for 2 h;Ionic liquid;Reagent/catalyst;Solvent;

Steps:

Esterification in IL or in Molecular Solvents

The amount of 0.3 g of IL was weighed in a screw-capped 3-ml vial, equipped with a magnetic stirrer; thereafter, the carboxylic acid was added, and then the amine was introduced by a syringe (TEA=benzoic acid1.2:1.0). The mixture was magnetically stirred and heated to 90 C until a clear colorless liquid phase was obtained. Finally, benzyl chloride (BnCl=benzoic acid 1.1:1 molar ratio) was added by means a syringe to the homogenous mixture. At the end of reaction, after cooling to rt, water and ethyl ether were added to the reaction mixture, and the mixture was transferred as quantitatively as possible (rinsing with both water and ethyl ether were carried out) to a separatory funnel, where also t-butylbenzene was added, as internal standard. The organic phase was washed twice with water (10mL), twice with NaHCO3 solution, and twice with 3M HCl, and with water again until neutrality; it was thereafter dried over anhydrous Na2SO4 and analyzed by GLC. For reaction in traditional molecular solvents, the amount of 1 mmol of carboxylic acid was weighed in a screw-capped 5-ml vial, equipped with a magnetic stirrer, and then 3mL of solvent were added. Thereafter, the amine, in the chosen molar ratio, was introduced by a syringe. The homogeneous mixture was magnetically stirred and heated to 90 C. Finally, benzyl chloride (BnCl=carboxylic acid 1.1:1 molar ratio) was added by means a syringe to the homogenous mixture. Further elaboration was as described previously.

References:

Cardellini, Fabio;Brinchi, Lucia;Germani, Raimondo;Tiecco, Matteo [Synthetic Communications,2014,vol. 44,# 22,p. 3248 - 3256]

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