RU1235148C - Method of obtaining arylchlorformate - Google Patents

Description

2YUTO1 / sos1g or 2 GoTo1sShitoGotoTo;, h-SG

where R is Me.

taken in amounts of 0.5-3.0 mol. % in terms of

on substituted pyridine W-oxide from raceon

per 1 hydroxyl group of the starting phenol, and the process is carried out at 20-60 ° C.

,,.

The invention relates to the field of organic chemistry, in particular to a method for producing chemical plant protection products. The disclosed compounds are also useful as intermediates in the pharmaceutical industry and in the manufacture of plastics.

The aim of the invention is to increase the yield of the target product, simplification of technology and process intensification.

EXAMPLE 1 To a reactor equipped with a thermostatic jacket, stirrer, thermometer, reflux condenser and tube for phosgene injection, 144 g of {1 mol) of 1-naphthol, 300 m of chlorobenzene are charged and the reaction mixture is saturated with phosgene at a temperature of b ° C. then a solution of 3 g (0.027 mol) of M-oxide-4-methyl-pyrmdine (2.7%) in 50 ml of chlorobenzene is added. Phosgene was fed continuously for 2.5 hours at a rate of 30 g / h. Excess phosgene is then removed from the reaction mass by purging with nitrogen. After the solvent is removed by vacuum, a white crystalline hygroscopic complex of the composition drops out from the raster: 1 mol of phosgene per 2 mol of N-oxi-4-methylpyrilda a. which, after filtration, can again be used as a catalyst, Ф-. Ltrate is 1-naphthyl chloroformate. The yield of 204 g (99.37i) contained 98% of the basic substance.

Example 2. 4.4 g (0-.014 mol) of the complex obtained in Example 1. are dissolved in 350 ml of chlorobenzene, 144 g (1 mol) of T-naphthol are added and, similarly to the example, they are reacted with phosgene. The yield of 1-naphthylchloroformate is 203.5 g (99%), the content of the basic substance is 98%. The precipitate after filtration can again be used as a catalyst in phosgeneration.

Example 3. In the device, og. In Example 1, 94 g (1 mol) of Phenall, 200 ml of carbon tetrachloride are charged, the reaction mixture is nasic with phosgene and a solution of 2.5 g (0.026 mol) of pyridine N-oxide (2.6%) in 20 ml of carbon tetrachloride is added. Phosgene is supplied continuously for 3 hours at a rate of 30 g / h. The isolation of phenylchloroformate was carried out analogously to Example 1. Yield of the desired product 153.5 g (98.1%) with a purity of 98%.

Example 4. The reaction was carried out as described in Example 3, but 3.5 g (0.026 mol) of M-pyridine chlorohydrate (2.6%) were used as a catalyst. The yield of the target product 154.8 g (98.2%) with a purity of 98%,

PRI me R 5. Dissolve 2.5 g

(0.026 mls) of pyridine M-oxide in 10 mp benzene and 2 g of phosgene are added at room temperature. In this case, a white crystalline oyadok of a complex with a composition of 0.5 mol of phosgene per 1 mol of N-oxide

pyridine. Benzene with an excess of phosgene is distilled off in vacuo, the residue is used as a catalyst, as described in Example 3, The yield of the whole product i5, 2 g (98.1%) with a purity of 98%,

EXAMPLES 6-64. Reactions were carried out as described in R Examples 1, 4, 5. The loading of phenols, catalysts and solvents, the time and temperature of the process, and the yield of the target product are shown in the table.

(56) U.S. Patent 40 No. 3170946, chl, 260-463, published, 1965,

USSR patent No. 527132. cl. C 07 C 69/96, 1972.

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The hydroxy hydroxyl group of phenol, calculated on the basis of N-oxide of substituted pyridne.

Editor G. Gerasimova

Compiled by I. Kovalev Tehred M. Morgenthal

Order 3183

Circulation

NGO Search for Rospatent 113035. Moscow, Zh-35, Rauska nab., 4/5

Production and Publishing Plant Patent, Uzhhorod. Gagarina St., 101

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Proofreader O. Gusti