4-propan-2-ylcyclohexan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 25 mL round bottom flask was added ethyl 1-((6-hydroxynaphthalen-2-yl)methyl)piperidine-4-carboxylate (313 mg, 0.1 mmol, 2 eq), 4-isopropylcyclohexanol (284 mg, 0.2 mmol, 2 eq), PPh3 (562 mg, 0.2 mmol, 2 eq) and dry toluene (0.5 mL) under N2. Then DIAD (404 mg, 0.2 mmol, 2 eq) was quickly added in one portion at room temperature. The reaction mixture was stirred at rt for 0.5 h. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (PE:EA=4:1) to give ethyl 1-((6-(4-isopropylcyclohexyloxy)naphthalen-2-yl)methyl)piperidine-4-carboxylate (213 mg, yield: 51%) as slight yellow oil. ESI-MS (M+1)+: 438.1. 1H NMR (400 MHz, CDCl3) δ: 7.64-7.57 (m, 3H), 7.36 (d, J=8.4 Hz, 1H), 7.10-7.08 (m, 2H), 4.60-4.58 (m, 1H), 4.05 (q, J=7.2 Hz, 2H), 3.56 (s, 2H), 2.85-2.81 (m, 2H), 2.07-2.04 (m, 1H), 2.01-1.97 (m, 2H), 1.83-1.71 (m, 4H), 1.51-1.40 (m, 6H), 1.24-1.15 (m, 6H), 1.11-1.06 (m, 1H), 0.83 (d, J=6.4 Hz, 6H). The solvent was removed under reduced pressure the residue was purified by silica gel column chromatography (PE:EA=4:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 1247 g of 4-isopropylcyclohexanol at 143°-150° C. was added in 6 hrs a mixture of 71.1 g (1.0 m) acrylic acid, 142 g (1.0 m) 4-isopropylcyclohexanol and 14.6 g (0.1 m) di-tert-butylperoxide. After an additional hour at 143°-150° the mixture was distilled at reduced pressure yielding 142.1 g. Bp:125°-141° C. (1.0 mm Hg). Odor:woody, milky-lactone, dry. Analysis:99% pure by VPC: 44% cis (odor:nonalactone, celery-lactone) 56% trans (odor:strong woody, cinnamic, urine) After an additional hour at 143°-150° the mixture was distilled at reduced pressure yielding 142.1 g Odor:woody, milky-lactone, dry

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 25 mL round bottom flask was added ethyl 1-((6-hydroxynaphthalen-2-yl)methyl)piperidine-4-carboxylate (313 mg, 0.1 mmol, 2 eq), 4-isopropylcyclohexanol (284 mg, 0.2 mmol, 2 eq), PPh3 (562 mg, 0.2 mmol, 2 eq) and dry toluene (0.5 mL) under N2. Then DIAD (404 mg, 0.2 mmol, 2 eq) was quickly added in one portion at room temperature. The reaction mixture was stirred at rt for 0.5 h. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (PE:EA=4:1) to give ethyl 1-((6-(4-isopropylcyclohexyloxy)naphthalen-2-yl)methyl)piperidine-4-carboxylate (213 mg, yield: 51%) as slight yellow oil. ESI-MS (M+1)+: 438.1. 1H NMR (400 MHz, CDCl3) δ: 7.64-7.57 (m, 3H), 7.36 (d, J=8.4 Hz, 1H), 7.10-7.08 (m, 2H), 4.60-4.58 (m, 1H), 4.05 (q, J=7.2 Hz, 2H), 3.56 (s, 2H), 2.85-2.81 (m, 2H), 2.07-2.04 (m, 1H), 2.01-1.97 (m, 2H), 1.83-1.71 (m, 4H), 1.51-1.40 (m, 6H), 1.24-1.15 (m, 6H), 1.11-1.06 (m, 1H), 0.83 (d, J=6.4 Hz, 6H). The solvent was removed under reduced pressure the residue was purified by silica gel column chromatography (PE:EA=4:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 1247 g of 4-isopropylcyclohexanol at 143°-150° C. was added in 6 hrs a mixture of 71.1 g (1.0 m) acrylic acid, 142 g (1.0 m) 4-isopropylcyclohexanol and 14.6 g (0.1 m) di-tert-butylperoxide. After an additional hour at 143°-150° the mixture was distilled at reduced pressure yielding 142.1 g. Bp:125°-141° C. (1.0 mm Hg). Odor:woody, milky-lactone, dry. Analysis:99% pure by VPC: 44% cis (odor:nonalactone, celery-lactone) 56% trans (odor:strong woody, cinnamic, urine) After an additional hour at 143°-150° the mixture was distilled at reduced pressure yielding 142.1 g Odor:woody, milky-lactone, dry