Novel aroma chemicals having a 1,2,2-trimethylcyclopentan-1-yl moiety
A technology of trimethylcyclopentyl and methyl, which is applied in the field of new aromatic chemicals with 1,2,2-trimethylcyclopentane-1-yl structural parts, and can solve the difficulty of exploring new flavors and fragrances , material difficulties, labor and other issues
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Embodiment 1
[0214] Example 1: (E)-2-methyl-4-(1,2,2-trimethylcyclopentyl)but-2-enal
[0215] To a mixture of 2-(1,2,2-trimethylcyclopentyl)acetaldehyde (10.0 g, 64 mmol) and propionaldehyde (10.0 g, 174 mmol) in 30 mL of isopropanol was added NaOMe 25% solution in MeOH (10 mL, 47 mmol). The resulting solution was stirred at 60°C for 10 hours. The reaction mass was cooled to RT and 30 mL of water was added. The reaction mass was extracted twice with 75 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine solution and dried over sodium sulfate. The solvent was removed under reduced pressure to give the crude title compound (8.0 g), which was used without further purification.
[0216] 1 H NMR CDCl 3 :δ9.35(s 1H),6.5(t 1H),2.2(d 2H),1.7(s 3H),1.7-1.4(6H),0.9-0.8(s 9H)
Embodiment 2
[0217] Embodiment 2: (E)-2-ethyl-4-(1,2,2-trimethylcyclopentyl)but-2-enal
[0218] To a mixture of 2-(1,2,2-trimethylcyclopentyl)acetaldehyde (6.5 g, 33 mmol) and butyraldehyde (8.0 g, 111 mmol) in 25 mL of isopropanol was added NaOMe 25% solution in MeOH (7.5 mL, 38 mmol). The resulting solution was stirred at 80°C for 10 hours. The reaction mass was cooled to RT and 30 mL of water was added. The reaction mass was extracted twice with 50 mL of ethyl acetate. The combined organic layers were washed with 50 mL of brine solution and dried over sodium sulfate. The solvent was removed under reduced pressure to give the crude title compound (8.0 g), which was used without further purification.
[0219] 1 H NMR CDCl 3 :δ9.35(s 1H), 6.5(t 1H), 2.2(d 2H), 1.7(q 2H), 1.7-1.4(6H), 0.9-0.8(s 9H), 0.8-0.75(s 3H).
Embodiment 3
[0220] Example 3: (E)-2-ethyl-4-(1,2,2-trimethylcyclopentyl)but-2-en-1-ol
[0221] Crude (E)-2-ethyl-4-(1,2,2-trimethylcyclopentyl) but-2-enal (8.0 g, 38 mmol) and methanol (25 ml) was cooled to 0°C and NaBH was added slowly 4 (1.5 g, 39 mmol). The reaction mass was stirred at 20°C for 30 minutes. 50 mL of water was added and the reaction mass was extracted twice with ethyl acetate (75 mL). The combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure to yield crude (E)-2-ethyl-4-(1,2,2-trimethylcyclopentyl)but-2-en-1-ol (6.5 g). The crude product was then purified by column chromatography to yield pure (E)-2-ethyl-4-(1,2,2-trimethylcyclopentyl)but-2-en-1-ol (1.2 g)
[0222] 1 H NMR CDCl 3 :δ5.4-5.45(t 1H), 3.95(s 2H), 2.2-2.1(q 2H), 2.0-2.2(d 2H), 1.7-1.4(6H), 1.0-0.95(t 3H), 0.9- 0.8(s 6H),0.8-0.75(s 3H).
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