2,6-Lutidine → Ethyl 4-formyl-3,3-dimethylbutanoate

HRID 653674Notes

Reaction equation

HRID 653674 reaction equation
[CH3:1][C:2]([CH3:11])([CH2:7][C:8]([OH:10])=O)[CH2:3][C:4]([OH:6])=[O:5].N1C(C)=CC=[CH:14][C:13]=1C>O1CCCC1.[Pd]>[CH:8]([CH2:7][C:2]([CH3:1])([CH3:11])[CH2:3][C:4]([O:6][CH2:13][CH3:14])=[O:5])=[O:10]

Participants

5

Reactant 2

HCID 79372,6-LutidineHCID 209843,3-Dimethylglutaric acid

Product 1

HCID 13050815Ethyl 4-formyl-3,3-dimethylbutanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

40 g of the acid chloride ethyl ester of 3,3-dimethylglutaric acid, prepared in Example 28, are dissolved in 400 ml of tetrahydrofuran. 2 of 5% palladium-on-charcoal and 22.8 ml of 2,6-lutidine are added and the mixture is hydrogenated at normal pressure and room temperature. When the absorption of hydrogen has ceased, the catalyst is filtered off and the solvent is evaporated off under vacuum. The residue is taken up with water and extracted with ether. The ether phase is washed with a dilute solution of hydrochloric acid in the cold, washed with a solution of sodium bicarbonate in the cold, dried over magnesium sulfate and evaporated under vacuum to give, after distillation of the residue, 18 g of ethyl 4-formyl-3,3-dimethylbutanoate in the form of a liquid with a boiling point b.p.20 of 112°-118° C.

Workup

  1. customis hydrogenated at normal pressure and room temperature
  2. customWhen the absorption of hydrogen
  3. filtrationthe catalyst is filtered off
  4. customthe solvent is evaporated off under vacuum
  5. extractionextracted with ether
  6. washThe ether phase is washed with a dilute solution of hydrochloric acid in the cold
  7. washwashed with a solution of sodium bicarbonate in the cold,
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under vacuum
  10. customto give
  11. distillationafter distillation of the residue, 18 g of ethyl 4-formyl-3,3-dimethylbutanoate in the form of a liquid with a boiling point b.p.20 of 112°-118° C.

Sources & evidence

ORD record
ord-114ddf24bcb14bed83155c9b9b651a4e
Source dataset
uspto-grants-1992_07
Patent number
US05128359

Reaction notes

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