CH231663A - Process for producing a chroman compound. - Google Patents

Description

  

  Process for the preparation of a cliroman compound. The subject of the present patent is a process for the production of a chroman compound which is characterized in that 4-formylamino-2,3,5-trimethyl-pheno @ l with 3-methyl-3-n-tridecyl-l -brom- propen- (2), condensed and in, the product obtained in this way the in the 6-,

  The FoTmylaminooTuppe in position is saponified and the amino group obtained is converted into the oxygroup via the diazo compound.

   The product that can be obtained in this way, 6-oxy-2,5, 7,8-tetramethyl-2-tridecyl-chroman, is a pale yellow oil that solidifies to a yellowish-white crystal mass when rubbed, which melts at 58. It is intended to be used as a medicinal product.



  <I> Example: </I> 5 g 4 - formylamino - 2,3,5 - trimethyl - pheno # l, 8 .g 3-methyl - 3-n-tridecyl-l-bromo- propen- (2) and 3 .g interest rate chloride, in 100 cm? L groin heated to 85 for 3 hours while stirring and passing a stream of nitrogen through. The evolution of hydrogen bromide then ceased.

   After cooling, the reaction mixture is filtered off from a very small residue and the filtrate is evaporated to dryness under reduced pressure. The viscous residue is dissolved in 100 cm of alcohol and 20 g of potassium hydroxide are added to the solution, a white precipitate of zinc salts immediately separating out.

   The alcoholic solution is heated to the boil for several hours with the Niedersühdag, then filtered and the filtrate is mixed with petroleum ether and a little water.

   After the petroleum ether layer has been separated off, the alcoholic aqueous layer is extracted twice with petroleum ether and the combined extracts are washed with water, dried and evaporated. The residue is distilled in vacuo and, after a short run, turns over as a yellow oil which boils at 2.38 and 0.2 mm pressure.

   The distillate solidifies to a yellowish white crystal mass with a melting point of 51. Redissolving from 85% alcohol gives the 6-amino-2 ", 7,8-tetramethyl-2-tridecyl-Ehroman in colorless, fatty flakes with a melting point of 53.

   The absorption spectrum of the compound shows a maximum at 310 mIt and is almost identical. with that of 6-amino tocol.



  If the reaction mixture is worked up before saponification, 6-formylamino-2,5,7,8-tetramethyl-2-tri-decyl-Ehroman with a melting point of 97 is obtained.



  The 6-amino compound is converted into the 6-oxy compound in the following manner, for example.



  1.93 g of 6-amino-2,5,7,8-tetramethyl-2-t @ ridecylchro: one is dissolved in 50 cubic meters of glacial acetic acid and 2 cm3 of 50% sulfuric acid and, with cooling, with a solution of 0 ,

  36 g of sodium nitrite diazotized in 2 cm of water. A small excess of nitrous acid is destroyed with sulfamic acid and the diazole solution is then poured into a boiling mixture of 150 cm 3 of water, 70 cm 3 of sulfuric acid and 50 cm 3 of chlorobenzene while stirring and bubbling through with nitrogen.

   The decomposition of the diazo group takes place with upsetting. After a boiling time of 10 minutes, the mixture is cooled: the chlorobenzal layer is separated off, diluted with a little petroleum ether, the mixture is extracted twice with 'as;: cr, dried and the solvent is evaporated.

   The residue is distilled in a high vacuum and changes to an orange-yellow oil with a boiling point of 215-220 under 0.1 mm pressure. After two distillation, the 6-oxy-2,5,7,8-tetra-methyl-2-tridecyl-chromane is obtained as a light yellow oil which solidifies to a yellowish-white crystal mass which melts at 58 when rubbed.

 

Claims (1)

PATENT CLAIM: Process for the production of a chroman compound, characterized in that 4 - formylamino - 2,3,5 - trimethylphenol with 3-3lethy l-3-n-tridecyl-1-bromo-propen- (2) condenses and in the product thus obtained, the formylamino group in the 6-position is saponified and the amino group obtained is converted into the oxy group via the dia.zo compound. The new product thus obtainable is a light yellow 01, which solidifies to a yellowish, white crystal mass when rubbed, which melts at 58.