Method for synthesizing (S)(-)-gamma-lactone
A synthesis method and lactone technology are applied in the field of preparation of chiral synthetic fragrances, can solve problems such as no reports, and achieve the effects of improving economic value and improving aroma quality
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[0006] Example one
[0007] In a 50 ml three-necked flask, 2.4 g (60 mmol) of sodium hydroxide was dissolved in 20 ml of water, and 6.8 g (40 mmol) of racemic γ-decanolide was added dropwise at 60°C. Stirring was continued for 2 hours at temperature. After cooling to room temperature, add 20 ml of ethyl acetate, and then add 20% sulfuric acid dropwise to adjust the acidity to P H = 5. The organic layer was extracted and separated, and extracted twice with ethyl acetate. The organic layers were combined, and 2.4 g (20 mmol) of (R)-(+)-α-phenethylamine was added. This solution was cooled at -15~-30°C for 48 hours to obtain 2.5 g of white crystals. This crystal was dissolved in 10 ml of water and heated to 90°C. When all the solids were dissolved, dilute sulfuric acid was added to obtain a hydroxy acid which was further cyclized into a lactone. It was extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, and the solvent was removed to obtain (S)-...
Example
[0008] Example two
[0009] In a 1000 ml three-necked flask, 38.4 g (960 mmol) of sodium hydroxide was dissolved in 320 ml of water, and 108.8 g (640 mmol) of racemic γ-decanolide was added dropwise at 60°C. Stirring was continued for 2 hours at temperature. After cooling to room temperature, add 320 ml of ethyl acetate, and then add dropwise 20% sulfuric acid to adjust the acidity to P H = 5. The organic layer was separated and extracted twice with ethyl acetate. The organic layers were combined, 128 ml of methanol was added, and 38.7 g (320 mmol) of (R)-(+)-α-phenethylamine was added. This solution was cooled at -22°C for 18.5 hours to obtain 65.0 g of white crystals. This crystal was dissolved in 100 ml of water and heated to 90°C. When the solid matter was completely dissolved, dilute sulfuric acid was added to obtain a hydroxy acid which was further cyclized into a lactone. It was extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, and ...
Example
[0010] Example three
[0011] In a 1000 ml three-necked flask, 38.4 g (960 mmol) of sodium hydroxide was dissolved in 320 ml of water, and 108.8 g (640 mmol) of racemic γ-decanolide was added dropwise at 60°C. Stirring was continued for 2 hours at temperature. After cooling to room temperature, add 320 ml of ethyl acetate, and then add dropwise 20% sulfuric acid to adjust the acidity to P H = 5. The organic layer was separated and extracted twice with ethyl acetate. The organic layers were combined, 128 ml of methanol was added, and 38.7 g (320 mmol) of (R)-(+)-α-phenethylamine was added. This solution was cooled at -22°C for 67.5 hours to obtain 60.0 g of white crystals. This crystal was dissolved in 50 ml of water and heated to 80°C. When the solid matter was completely dissolved, it was lowered to room temperature, and 55.0 g of solid was obtained by suction filtration.
[0012] Dissolve the recrystallized solid in an appropriate amount of water and heat it to 90°C. When the so...
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