Esters and ethers of 3-methyl-pentane-diol and unsaturated derivatives thereof and their use as aroma chemical
A technology for synthesizing perfumes and uses, which is applied in the direction of detergent composition perfumes, dehydration of hydroxyl-containing compounds to prepare ethers, essential oils/perfumes, etc., and can solve the problems of not describing the use of synthetic perfumes, etc.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0761]
[0762]
[0763] DMAP was added to a THF solution of citral s.s. diol mixture at RF. The mixture was brought to reflux (53°C) and acetic anhydride (2.25 equiv) was added slowly at this temperature. After 1 hour, 99% diol conversion was observed by GC. The reaction was cooled to room temperature and quenched slowly with 100 mL of water, then 100 mL of ethyl acetate was added. The organic phase was separated and washed with NaHCO 3 Wash with saline solution. The organic extracts were combined and dried over sodium sulfate. After evaporating the solvent under reduced pressure, 37.1 g of crude product containing about 90% diacetate (according to GC area %) were obtained. The product was purified by distillation. The corresponding diacetate mixture was obtained in a purity of 93.2% (GC area %). NMR confirmed the composition of the mixture to be a 1:1 E / Z mixture of 50% 3-methylene diacetate and 50% 2-pentene derivative.
[0764]
[0765]
[0766]
[07...
Embodiment 2
[0769] -
[0770]
[0771]Formic acid was slowly added to acetic anhydride at 0 °C. The mixture was stirred at 55°C for 1.5 hours, then the mixture was cooled to 0°C and 50 mL of THF was added. At this temperature, a solution of the citral s.s. diol mixture in 50 mL THF was slowly added, followed by the addition of DMAP to the mixture. The reaction was stirred at room temperature for 4 hours, complete conversion was observed by GC. 100 mL of toluene was added to the mixture, and the organic phase was washed 3 times with 30 mL of water. The organic phase was dried over sodium sulfate and the solvent was removed in a rotary evaporator to give 19.6 g of crude product containing about 90% diformate according to GC (area %). The product was purified by distillation. The corresponding mixture of dicarboxylates was obtained in a purity of 98.1% (GC area %). NMR confirmed the composition of the mixture to be a 1:1 E / Z mixture of 50% 3-methylene dicarboxylate and 50% 2-penten...
Embodiment 3
[0775]
[0776]
[0777] A solution of citral s.s. diol mixture, triethylamine and DMAP in hexane was cooled to 0°C. At this temperature, propionyl chloride was slowly added. The reaction was stirred at room temperature for 1 hour, 50 mL of hexane was added, and the reaction was stirred at reflux (67 °C) for 4 hours. After this time complete conversion was observed by GC. The reaction was cooled to room temperature and quenched slowly with 100 mL of water, 100 mL of ethyl acetate was added, and the organic phase was washed with NaHCO 3 Wash with saline solution. The organic extracts were combined and dried over sodium sulfate. After evaporating the solvent under reduced pressure, 38.4 g of crude product containing about 90% dipropionate (according to GC area %) were obtained. The product was purified by distillation. The corresponding mixture of dipropionates was obtained in a purity of 97.8% (GC area %). NMR confirmed the composition of the mixture to be a 1:1 E / Z...
PUM
| Property | Measurement | Unit |
|---|---|---|
| melting point | aaaaa | aaaaa |
| temperature | aaaaa | aaaaa |
| melting point | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
Login to View More