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

HRID 619315Notes

Reaction equation

HRID 619315 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

Reactant 1

HCID 218467092-(hex-1-ynyl)-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene

Product 1

HCID 218467162-hexyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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%).

Workup

  1. filtrationFiltration
  2. customover diatomaceous earth and removal of the solvent

Sources & evidence

ORD record
ord-eca8ed0b96de48a58607fc0b3b9590fb
Source dataset
uspto-grants-1999_09
Patent number
US05958956

Reaction notes

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