Triethylamine → HCID 178445615, compound

HRID 1982112Notes

Reaction equation

HRID 1982112 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH:11]=[CH:12][CH:13]2OCC[O:14]2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C>C(O)C.[Pd]>[CH2:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH2:11][CH2:12][CH:13]=[O:14])[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178445609HCID 178445609, compound

Product 1

HCID 178445615HCID 178445615, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The crude trans-4-butyl-1-[2-(1,3-dioxolan-2-yl)-vinyl]cyclohexane obtained is dissolved in 500 ml of ethanol, treated with 1 ml of triethylamine and 1 g of palladium/carbon (5%) and hydrogenated while shaking. After completion of the hydrogen uptake, the mixture is filtered and the residue is rinsed with 100 ml of ethanol. The filtrate is concentrated to half volume on a rotary evaporator, treated with 300 ml of water and 5 ml of concentrated sulphuric acid and heated to 80° C. for 30 minutes. For the working-up, the mixture is diluted with water, neutralized with sodium hydrogen carbonate and extracted twice with 250 ml of tert.butyl methyl ether each time. The organic phases are dried over sodium sulphate and freed from solvent on a rotary evaporator. The crude product of 3-(trans-4-butylcyclohexyl)propanal obtained is distilled in a high vacuum.

Workup

  1. filtrationAfter completion of the hydrogen uptake, the mixture is filtered
  2. washthe residue is rinsed with 100 ml of ethanol
  3. concentrationThe filtrate is concentrated to half volume on a rotary evaporator
  4. additiontreated with 300 ml of water and 5 ml of concentrated sulphuric acid
  5. additionthe mixture is diluted with water
  6. extractionextracted twice with 250 ml of tert.butyl methyl ether each time
  7. dry with materialThe organic phases are dried over sodium sulphate
  8. customfreed from solvent on a rotary evaporator

Sources & evidence

ORD record
ord-638fae669b0f4b5292eecb4e9b990a8b
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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