The way to obtain benzyl benzoate

 

(57) Abstract:

The invention relates to the synthesis of biologically active chemical compounds and can be implemented in pharmacology, medicine and agriculture. The benzyl benzoate is produced by interaction of benzyl alcohol with benzoyl chloride in aqueous-alkaline solution, and the process is initially carried out at 13-16oC for 1.0 to 1.5 hours, then further introduced into the system sodium hydroxide in a molar ratio of (1.9 to 2.1 a) benzoyl chloride, incubated the mixture at 16-18oWith over 0,8-1,2 h, heat the resulting reaction mass to 50-60oC and maintain it at this temperature for 1.0 to 1.5 hours Out of benzoylbenzoate increases up to 95-97%. table 1.

The present invention relates to the field of synthesis of biologically active chemical compounds and can be implemented in pharmacology, medicine and agriculture.

A method of obtaining benzyl benzoate by liquid-phase interaction of benzoyl chloride with sodium benzoate in the aquatic environment. The disadvantages of this known method are the relatively low yield of the target product, the need to clean it from escaping during the reaction byproduct is that [F. Gomberg, A. Bucheer. J. Amer.Chem.Soc., 1920. V. 42, P. 2059].

A method of obtaining benzyl benzoate by the esterification of benzoic acid benzyl alcohol in the presence of 1-fluoro-2,4,6-trinitrobenzene and 4-(dimethylamino) pyridine in acetonitrile [S. Kim. Synth.Commun., 1981, V. 11, P. 121]. This method, however, requires the use of very expensive, scarce and also toxic reagents. Another drawback is the relatively low (but greater than the yield of the target product [F. Gomberg, A. Bucheer. J. Amer. Chem. Soc., 1920. V. 42, P. 2059].

Closest to the claimed us the object on the totality of symptoms and the achieved technical effect is a method for benzyl benzoate by liquid-phase interaction of benzyl alcohol with benzoyl chloride in acetonitrile in the presence of inorganic compounds of zinc chloride (II) at room temperature. The disadvantage of this method is the relatively low yield of the target product. In addition, in this case, the synthesis process requires the use of an organic solvent is acetonitrile, and additional purification of the final product from the impurities of Zn-containing compounds, which complicates the process of obtaining [S. Kim, W. Le is the output of the target product benzyl benzoate and simplify the process of obtaining.

This objective is achieved in that in the known method [S. Kim, W. Lee, J. Lee. Bull. Korean Chem. Soc., 1984, V. 5, p. 187; Chemical Abstracts, 1985, 102, N 166418] obtain benzyl benzoate by liquid-phase interaction of benzyl alcohol with benzoyl chloride in the presence of inorganic compounds in the solvent used water, as well as inorganic compounds sodium hydroxide, the process is initially carried out at 13-16oC for 1.0 to 1.5 hours, then further introduced into the system sodium hydroxide in a molar ratio of (1.9 to 2.1 a) benzoyl chloride, incubated the mixture at 16 - 18oC for 0.8 to 1.2 hours, heat the resulting reaction mass to 50 - 60oC and maintain it at this temperature for 1.0 to 1.5 hours. As a result, the yield of the target product increases (85 - 87)% $ (95 - 97)% while simplifying the technological process, as the need for any additional purification of the obtained product disappears.

Previously, the way to obtain benzyl benzoate with item above set of features in the literature was not described. This circumstance allows us to assert that the claimed us abjectly, - novelty. In addition, knowledge of the known characteristics of the prototype method [S. Kim, W. Lee, J. Lee. Bull. Korean Chem. Soc., 1984, V. 5, p. 187; Chemical Abstracts, 1985, 102, N 166418] and the combination of features made changes to it (namely the replacement of the solvent and of zinc chloride to sodium hydroxide, using a molar ratio (Oh/benzoyl chloride), exactly equal to 1.9 and 2.1, and the above temperature-time mode synthesis) is not possible a priori to predict the achievement of the above technical result, namely to increase the yield of the target product. In this regard, there is every reason to believe that the entity declare our object is not obvious from the currently known level in the relevant field of technology and that it falls under the second criterion characteristic of the patent law of the Russian Federation - an inventive step.

Finally, we state our method is simple to perform, does not require for their implementation of any specific, expensive or toxic reagents, which is not produced if the domestic industry, and therefore is fully realizable in the laboratory and on an industrial scale. In this regard, it is safe to say that we declare our object falls under tray benzyl benzoate is demonstrated by the following examples.

EXAMPLE 1

In a three-neck flask with a capacity of 5.0 liters, equipped with a stir bar, separating funnel, thermometer and bath for cooling and heating of the reaction mass, injected with 1.2 l of 20% aqueous sodium hydroxide solution and 0.55 l of benzyl alcohol. This mixture is stirred for 1 hour at room temperature and then cooled to 0oC. To the thus prepared suspension add 0.75 l of benzoyl chloride with such speed that the temperature of the mixture did not exceed 13oC. Upon completion of this procedure, the mixture is maintained at 13oC for 1.5 h, with constant stirring, then give it another 1.0 l of 20% aqueous NaOH solution, thereby establishing the molar ratio of sodium hydroxide/benzoyl chloride, equal to 1.9, and increase the temperature until 16oC. At this temperature and continuous stirring, the mixture was incubated for 1.2 hours and then heated it up to 50oC and maintained at this temperature for 1.5 hours under stirring. Next, the mixture is left to stand until complete separation, separating the upper layer and washed five times with water portions 1 l each wash. The resulting product is distilled in vacuum, collecting the fraction with tempey in table 1.

EXAMPLE 2

Perform as example 1, but the molar ratio of sodium hydroxide/benzoyl chloride set equal to 2.0, and the mixture incubated at 15oC for 1.2 hours, 17oC for 1.0 hour and at 55oC for 1.2 hours.

EXAMPLE 3

Carried out like example 1, but the molar ratio of sodium hydroxide/benzoyl chloride set equal to 2.1, and the mixture was incubated at 16oC for 1.0 hour, 18oC for 0.8 hour and at 60oC for 1.0 hour.

EXAMPLE 4 (comparative)

Conduct and as example 1, but the molar ratio of sodium hydroxide/benzoyl chloride set equal to 1.7.

EXAMPLE 5 (comparative)

Conduct and as example 1, but the molar ratio of sodium hydroxide/benzoyl chloride set equal to 2.3.

EXAMPLE 6 (comparative)

Carried out like example 1, but the mixture was incubated at 16oC for 2.0 hours, 18oC for 2.0 hours and at 60oC for 2.0 hours.

EXAMPLE 7 (comparative)

Carried out like example 1, but the mixture is maintained at 20oC for 1.0 hour, 24oC for 0.8 hour and at 60oC for 1.0 hour.

EXAMPLE 8 (comparative)

Carried out like example 1, no.

EXAMPLE 9 (comparative)

Carried out like example 1, but the mixture was incubated at 16oC for 1.0 hour, 18oC for 0.8 hour and at 50oC for 0.5 hour.

EXAMPLE 10 (comparative)

Carried out like example 1, but the mixture was incubated at 16oC for 0.5 hour, 18oC for 0.5 hour and at 60oC for 1.0 hour.

EXAMPLE 11 (comparative)

Carried out like example 1, but the mixture is maintained at the 12oC for 1.0 hour, 15oC for 0.8 hour and at 40oC for 1.5 hour.

EXAMPLE 12 (prototype [S. Kim, W. Lee, J. Lee. Bull. Korean Chem.Soc., 1984, V. 5, P. 187; Chemical Abstracts, 1985, 102, N 166418]).

A mixture of 108 g of benzyl alcohol, 143 g of benzoyl chloride and 17.2 g of zinc chloride (II) was injected in 0.5 ml of acetonitrile and stirred for 6 hours at room temperature. Then the reaction was poured into water and extracted the product of the reaction with benzene. The obtained benzene solution is washed with water, dried with magnesium sulfate, then the solvent is distilled off and the residue is distilled in vacuum. In the process of distillation, collecting the fraction with a boiling point of 184-185oC (15 mm RT.cent.).

Data on the yield of the target product for the specified case is also presented in table 1.

The way to obtain benzyl benzoate by liquid-phase interaction of benzyl alcohol with benzoyl chloride in the presence of a solvent and inorganic compounds, characterized in that the solvent used water as inorganic compounds - sodium hydroxide, the process is initially carried out at 13 - 16oC for 1.0 to 1.5 h, then further introduced into the system sodium hydroxide in a molar ratio of 1.9 to 2.1 for benzoyl chloride, incubated the mixture at 16 - 18oC for 0.8 - 1.2 hours, heat the resulting reaction mass to 50 - 60oC and maintain it at this temperature for 1.0 to 1.5 hours

 

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,

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12 cl, 1 dwg, 6 tbl, 8 ex

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EFFECT: invention has the following advantages: 3-5 times shorter duration of the condensation process; 1,6 times increase in output of the product; avoiding preparatory operations associated with absolutisation of pyridine; considerably shorter duration and labour input in purification.

1 tbl, 13 ex

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