HCID 20035406, compound → HCID 20035400, compound

HRID 1905353Notes

Reaction equation

HRID 1905353 reaction equation
[CH:1]([CH:4]1[CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]([CH3:15])[CH:7]=[CH:6][CH2:5]1)([CH3:3])[CH3:2]>[Pd].C(O)C>[CH:1]([CH:4]1[CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 20035406HCID 20035406, compound

Product 1

HCID 20035400HCID 20035400, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.5 g of 5% palladium on charcoal as a catalyst was added to 10.5 g of ethyl 6-isopropyl-2-methyl-3-cyclohexene-1-carboxylate (mixture of isomers obtained according to Example 1) dissolved in 100 ml of ethanol, after which the mixture was hydrogenated at 20° C. for 1 hour under a hydrogen pressure of 100 kPa. The catalyst was then filtered off, the filtrate evaporated down and the evaporation residue distilled. 9.4 g of the desired compound were obtained as a mixture of the cis-trans and the trans-trans isomer. b.p.: 96°-97° C./1 kPa; NMR (of the mixture): 0.7-1.0 (9H); 1.24 (3H, t); 1.0-2.5 (10H); 3.9-4.2 (2H).

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe filtrate evaporated down
  3. distillationthe evaporation residue distilled

Sources & evidence

ORD record
ord-ba9c9993a9374c13966fceb738cd9199
Source dataset
uspto-grants-1989_06
Patent number
US04843061

Reaction notes

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