DE2521700A1 - BETA, BETA-DIACYLOXY- (OR BETA, BETA-DIARYLOXY-) AETHANOLS AND THE PROCESS FOR THEIR PRODUCTION - Google Patents

Description

concerning:

" ß ^ ß-Diacyloxy-C or ß, ß-Diaryloxy-) ethanols and process for their preparation "

The invention relates to a series of new chemical compounds, namely the β, β-diacyloxy (or β, β-diaryloxy) ethanols as well as a process for their production "

The invention relates to a new class of chemical compounds, which is represented schematically by the following general formula can be represented:

OH

OH.

OH

OCOX ¹

wherein X and X ¹ , which can be identical or different, are alkyl, arylalkyl, aryl or cycloalkyl radicals. The compounds of the invention are used for various

509847/1 181

252170 above

Purposes used, e.g. for the production of glycolaldehyde (by. Hydrolysis), which in turn is an intermediate product for the synthesis of solvents, plastics, d, (J-Serine etc. is. As for the rest of the production of d, ß-serine affects with the help of the Strecker reaction and its modifications takes place, this reaction can advantageously take place directly at the ß, ß-diacyloxy (or. ß, ß-Diaryloxy-) ethanols themselves are carried out, since the hydrolysis to aldehyde due to the alkaline conditions in the reaction itself takes place in situ.

The compounds mentioned are prepared according to the invention by reacting compounds of the formula:

OCOX

with a large excess of carboxylic acid of the type HOCOX '(HOCOX), in which X and X ^{1 have} the above meanings. The acids are used as such or, if appropriate, diluted with an inert solvent, for example a hydrocarbon, a halogenated hydrocarbon or an ether.

The vinyl ester epoxides used as starting material can can be obtained in a simple and economical way, e.g. with the help of in own patent applications methods described by the applicant.

The inventive process is carried out at temperatures between +5 and 100 ⁰ C, preferably at about 10 ° C, and the details will become apparent from the following example which, however, should not have a limiting sense.

7/1181

example

A solution of 1.02 g of vinyl acetate epoxide in 5 ml of glacial acetic acid was left to stand for 7 days at about 10 ° G in a closed flask. After this time has elapsed, an NMR (G ^ Dg) test carried out on the reaction mixture shows the only signals, apart from those for the acid, those which correspond to 2,2-diacetoxyethanol / "JfJ, 80 (d, 2H, CH ₂ ) and 7.05 ppm (t, 1H, OR) J and the presence of small amounts of a secondary product, monoacetoxyaldehyde / "cf4 ·, 15 (s> 2H, OH ₂ ) and 9 * 10 ppm (s, 1H, CHO) _7 can be attributed.

The reaction mixture is then diluted with 30 ml of methylene chloride and adds 7 g of sodium bicarbonate, whereupon the suspension is sealed against the humidity Stir vigorously for 3 hours at room temperature. This treatment allows for almost complete removal of acetic acid without loss of 2,2-diacetoxyethanol. The suspension is then filtered and the precipitate washed with a little methylene chloride. From the FiItrat is removed by evaporation in a rotary evaporator in addition to the methylene chloride, also the acetoxyacetaldehyde and any acetic acid that may still be present. The diacetoxyethanol obtained in this way can be further purified in the usual way.

PATENT CLAIMS:

5 0 9 8 U 7/1 1 8 1

Claims (1)

PATENT CLAIMS ß _} ß-diacyloxy (or ß, ß-diaryloxy) ethanols of the general formula: OH I CH, CH OCOX ¹ OCOX wherein X and X ¹ , which can be identical or different, are alkyl, arylalkyl, aryl or cycloalkyl radicals. (2) Process for the preparation of the compounds according to Claim 1, characterized in that a compound of the type: OCOX (X) with an excess of a carboxylic acid of the formula -. HOCOX ¹ (X), in which X and X ^{1 have} the above meaning , is implemented. Process according to Claim 1 or 2, characterized in that the reaction is carried out at a temperature between +5 and + 10O ⁰ C. (4-) Process according to claim 1, 2 or 3> characterized in that the reaction is carried out in the presence of an optionally halogenated hydrocarbon or an ether as the inert solvent. 86XXIV 509847/1181