ChemicalBook CAS DataBase List 1-METHYLADAMANTANE

1-METHYLADAMANTANE synthesis

15synthesis methods

Product Name:1-METHYLADAMANTANE
CAS Number:768-91-2
Molecular formula:C11H18
Molecular Weight:150.26

18220-83-2 Synthesis

18220-83-2
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768-91-2
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Yield: 78%

Reaction Conditions:

with 10 mol% palladium on carbon in cyclohexane at 130; for 48 h;Inert atmosphere;Molecular sieve;Sealed tube;

Steps:

Decarbonylation of 2-(adamantan-1-yl)acetaldehyde to 1-methyladamantane (2j)7
Dry glass reaction tube purged with argon and equipped with a magnetic stir bar was chargedwith molecular sieves (3-4 Å, 100 mg), aldehyde 1j (180 mg, 1.01 mmol), Pd/C (107 mg, 10mol% Pd), and cyclohexane (1 mL) and the sealed tube was heated at 130 °C for 48 h. The reaction mixture was cooled to room temperature, filtered through a pad of Celite, washed withCH2Cl2 (15 - 20 mL) and the solvents were removed under the reduced pressure. The crudeproduct was purified by dry-flash column chromatography (SiO2: pentane) to afford product 2j asa colorless powder (119 mg, 78 %).

References:

Ajdačić, Vladimir;Nikolić, Andrea;Kerner, Michael;Wipf, Peter;Opsenica, Igor M. [Synlett,2018,vol. 29,# 13,p. 1781 - 1785] Location in patent:supporting information