(L)-alpha-Terpineol → Dihydro-alpha-terpineol

HRID 1194903Notes

Reaction equation

HRID 1194903 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:4][CH:3]=1>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 443162(L)-alpha-Terpineol

Product 1

HCID 10353Dihydro-alpha-terpineolYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

α-Terpineol (6.17 g) in ethanol (130 ml) was hydrogenated for 1 h at atmospheric pressure using 10% Pd-C catalyst (290 mg). The catalyst was then removed by filtration through Kieselguhr and the solvent was removed under reduced pressure to leave the title compound as an oil (5.93 g). Distillation gave an oil (4.56 g) b.p. (13 mm) 98°; νmax (film) 3375, 2940, 1445, 1160, 1140, and 910 cm-1 ; δH (60 MHz, CDCl3) 0.6-2.0(m).

Workup

  1. customThe catalyst was then removed by filtration through Kieselguhr
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4b9d6171069e41a4b5afc1ec3971a343
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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