Ethyl Acetate → HCID 15904506, compound

HRID 1531601Notes

Reaction equation

HRID 1531601 reaction equation
[CH3:1][CH:2]1[CH2:3][C:4](=[O:19])[CH2:5][CH2:6][CH:7]([CH3:18])[CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17]1.C(OCC)(=O)C.[H][H]>[Pd].C(O)C>[CH3:1][CH:2]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([CH3:18])[CH2:6][CH2:5][C:4](=[O:19])[CH2:3]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 15904504HCID 15904504, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15904506HCID 15904506, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr bottle was charged with 3,14-dimethylcyclohexadeca-4E,12E-dien-one (0.203 g, 0.77 mmole), ethyl acetate (36 ml), ethanol (4 ml) and 5% palladium-on-carbon (0.050 g). The vessel was pressurized to 43 psi with hydrogen gas and the solution was shaken vigorously for 2 hours. The pressure was brought down to atmospheric pressure and the reaction mixture was filtered through a pad of Celite and the solvents were removed by distillation under reduced pressure to afford 3,14-dimethylcyclohexadecan-1-one (0.206 g, 100% yield). C18H34O (266.47 g/mole). 1HNMR (500 MHz, CDCl3): 0.861 (dd, 3H), 0.909 (dd, 3H), 1.38-1.03 (m, 20H), 1.62-1.38 (m, 3H), 2.10-1.98 (m, 1H), 2.18-2.11 (m, 1H), 2.43-2.33 (m, 3H) ppm. 13CNMR (125 MHz, CDCl3): 20.44, 20.80, 24.15, 25.21, 26.47, 26.50, 26.76, 27.06, 27.47, 29.10, 29.45, 31.31, 34.50, 35.61, 40.24, 50.48, 211.86 ppm. IR (νmax(cm−1)): 2930(s), 2910(s), 2856(s), 1713(s), 1460(s), 1412(w), 1375(m), 1146(w), 1096(w), 1059(w). MS (m/z): 266(M+), 251, 237, 223, 208, 152, 139, 125, 109, 97, 85, 69, 55, 41.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. customthe solvents were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-ac0d5ad079d04bdaa10955879d88d107
Source dataset
uspto-grants-2001_03
Patent number
US06200254B1

Reaction notes

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