METHOD FOR PRODUCING ADAMANTYL-CONTAINING CYCLIC KETALS Russian patent published in 2023 - IPC C07D317/72 

FIELD: organic chemistry.

SUBSTANCE: method for producing adamantyl-containing cyclic ketals used as flavors and fragrances for cosmetic products. Method for producing adamantyl-containing cyclic ketals of the formula

,

where X = H, Y = Z = CH₂ (1a); X = H, Y= CH₂, Z = CHMe (1b); X = H, Y = CH₂, Z = CHEt (1c); X = H, Y = CH₂, Z = CHPrⁿ (1d); X = H, Y = Z = CHMe (1e); X = H, -Y- Z- = -CH-(CH₂)₄-CH- (1f); X = H, Y= CH₂, Z = (CH₂)₂ (1h); X = H, Y= CMe₂CH₂, Z = CHMe (1i); X = H, Y= CH₂, Z = (CH₂)₃ (1j); X = OH, Y = CH₂, Z = CHMe (2b); X = OH, Y = Z = CHMe (2e), which can be used as fragrances and fragrances for cosmetic products. The method consists in the fact that in the case of obtaining ketal 1(a-j), catalytic condensation of 2-adamantanone with 1,2-ethanediol (a), or 1,2-propanediol (b), or 1,2-butanediol (c), or 1,2-pentanediol (d), or 2,3-butanediol (e), or cis -1,2-cyclohexanediol (f), or 1,3-propanediol (g), or 2-methyl-2 ,4-pentanediol (h), or 1,4-butanediol (j). In the case of obtaining ketal 2(b, e), catalytic condensation of kemantan with 1,2-propanediol (b) or 2,3-butanediol (e) is carried out. In this case, CuBr₂ is used as a catalyst, and the reaction is carried out for 1-3 hours at a temperature of 40-100^oC at a molar ratio of [ CuBr ₂ ] : [2-adamantanone or kemantan] : [diol] = 0.5-5 :100:100-300.

EFFECT: reduction in the duration of the reaction, a decrease in the synthesis temperature, a simplification of the method, and a reduction in the amount of waste.

1 cl, 1 tbl, 16 ex