HCID 45274958, compound → 2,6-Diethyl-5-isopropyl-2-methyltetrahydropyran

HRID 885770Notes

Reaction equation

HRID 885770 reaction equation
[CH2:1]([CH:3]1[O:8][C:7]([CH3:11])([CH:9]=[CH2:10])[CH2:6][CH2:5][CH:4]1[C:12]([CH3:14])=[CH2:13])[CH3:2].[H][H]>[Pd]>[CH2:9]([C:7]1([CH3:11])[CH2:6][CH2:5][CH:4]([CH:12]([CH3:13])[CH3:14])[CH:3]([CH2:1][CH3:2])[O:8]1)[CH3:10]

Participants

4

Reactant 2

HCID 45274958HCID 45274958, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 452749572,6-Diethyl-5-isopropyl-2-methyltetrahydropyranYield 63.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
90 °C

Procedure

The hydrogenation was carried out in a hydrogenation autoclave. 202 g of 6-ethyl-5-isopropenyl-2-methyl-2-vinyltetrahydropyran (from stage 1) were filled along with 8 g of Pd/active charcoal (Pd content: 5%) in the autoclave in the autoclave and hydrogenated at 30 bar hydrogen pressure. The reaction took place exothermically from 20° C. to approximately 50° C., after which heating to 90° C. was carried out. The H2 absorption was complete after 35 minutes. 107% of theoretical H2 was absorbed. The catalyst was filtered off and this was then rinsed with ethanol. The material obtained in this way was distilled via a 120 cm column. 131 g of 2,6-diethyl-5-isopropyl-2-methyl-tetrahydropyran (purity >97%) were obtained (73% of theoretical yield).

Workup

  1. customexothermically from 20° C. to approximately 50° C.
  2. customThe H2 absorption
  3. custom107% of theoretical H2 was absorbed
  4. filtrationThe catalyst was filtered off
  5. washthis was then rinsed with ethanol
  6. customThe material obtained in this way
  7. distillationwas distilled via a 120 cm column

Sources & evidence

ORD record
ord-1a9838045420411eb928e4cb7fa38734
Source dataset
uspto-grants-2012_08
Patent number
US08242289B2

Reaction notes

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