3-Methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol → HCID 14285247, compound

HRID 972172Notes

Reaction equation

HRID 972172 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH:8]1[CH2:12][CH:11]=[C:10]([CH3:13])[C:9]1([CH3:15])[CH3:14])[CH:3]([OH:5])[CH3:4].[H][H]>[Pd].C(O)C>[CH3:1][CH:2]([CH2:6][CH2:7][CH:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[C:9]1([CH3:15])[CH3:14])[CH:3]([OH:5])[CH3:4]

Participants

5

Reactant 2

HCID 1032123-Methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 14285247HCID 14285247, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 105 g (0.5 mole) of 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol, 5.3 g of 5% palladium on carbon and 100 ml of ethanol was hydrogenated at 30°-45° C and 35-50 psi until the hydrogen uptake ceased. The mixture was filtered to remove the catalyst and the solvent was removed from the filtrate by distillation. The residual oil was fractionally distilled to yield 3-methyl-5-(2,2,3-trimethylcyclopentan-1-yl)pentan-2-ol: 93.2 g (97.3% yield); bp 105°-107° C (1.3 mm); mol wt 212 (ms);

Workup

  1. customwas hydrogenated at 30°-45° C
  2. filtrationThe mixture was filtered
  3. customto remove the catalyst
  4. customthe solvent was removed from the filtrate by distillation
  5. distillationThe residual oil was fractionally distilled

Sources & evidence

ORD record
ord-95d4951e16db405ca83c2bfd6a519022
Source dataset
uspto-grants-1977_10
Patent number
US04052341

Reaction notes

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