Ambroxide synthesis
- Product Name:Ambroxide
- CAS Number:6790-58-5
- Molecular formula:C16H28O
- Molecular Weight:236.39
![Naphtho[2,1-b]furan, 1,2,3a,4,5,5a,6,9,9a,9b-decahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)-](/CAS/20210305/GIF/1038482-07-3.gif)
1038482-07-3
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6790-58-5
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Yield:6790-58-5 92%
Reaction Conditions:
with palladium 10% on activated carbon;hydrogen in methanol; under 760.051 Torr;
Steps:
I Compound 3 (AMBROX)
Compound 3 (AMBROX): Palladium on carbon (Pd/C, 10%, 5 mg) was added to compound 7 (25 mg 0.11 mmol) in MeOH (3 mL) and the resulting heterogeneous mixture was treated with H2 at 1 atm. The reaction mixture was filtered through celite and the residue was washed with methanol. The methanol was removed by a vacuum to yield the desired compound 3 (23 mg, 92%). The NMR data were identical with those of Zoretic P. A. et al. (Synthesis of d,l-Norlabdane Oxide and Related Odorants: An Intramolecular Radical Approach. J Org. Chem., 1998, 63(14): 4779-4785.). 1H NMR (400 MHz, CDCl3), δ 3.88-3.93 (m, 1H), 3.82 (q, J=8.4 Hz, 1H), 1.92-1.95 (m, 1H), 1.68-1.75 (m, 3H), 1.37-1.48 (m, 5H), 1.17-1.27 (m, 2H), 1.10 (s, 3H), 0.94-1.08 (m, 3H), 0.87 (s, 3H), 0.83 (s, 6H); 13C NMR (100 MHz, CDCl3), δ 80.0, 65.0, 60.1, 57.3, 42.5, 40.0, 39.8, 36.2, 33.6, 33.1, 22.6, 21.2, 20.7, 18.4, 15.1.
References:
US2016/46593,2016,A1 Location in patent:Paragraph 0033
515-03-7
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38419-75-9
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