2-(hex-1-ynyl)-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene → 2-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene
Reaction equation
[C:1]([C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]([CH3:18])([CH3:17])[C:11]=2[CH:19]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]([CH3:18])([CH3:17])[C:11]=2[CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Participants
4
Procedure
This alkyne was dissolved in 30 ml of ethy acetate and hydrogenated over 2 g of Pd/C (10%) at room temperature and under 1 atm H2. Filtration over diatomaceous earth and removal of the solvent gave 3.08 g of 2-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene as a colorless oil (GC purity: 98%).