Acetic Acid → HCID 12824183, compound

HRID 1722203Notes

Reaction equation

HRID 1722203 reaction equation
[C:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].[C:22](O)(=O)[CH3:23]>Cl.[Pd]>[C:2]1([CH2:1][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:22][CH3:23])=[O:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2988779-Benzoylnonanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 12824183HCID 12824183, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 26.15 g of 9-benzoylnonanoic acid in 260 ml of glacial acetic acid and 1 ml of 0.1N hydrochloric acid is hydrogenated (normal pressure) at 30°-35° C. with 2.6 g of palladium-on-charcoal (5% by weight) as catalyst. When no more hydrogen is taken up, the mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is dissolved in 200 ml of ethanol and 2 ml of concentrated sulfuric acid and the solution is refluxed for 22 hours. The solvent is evaporated off and the residue is treated with water and extracted with ether. The organic phase is separated off, washed with water, sodium bicarbonate solution (10% by weight) and saturated sodium chloride solution, dried and evaporated. Distillation of the residue under high vacuum (1 mbar, 137°-141° C.) gives 20 g of ethyl 10-phenyldecanoate.

Workup

  1. customat 30°-35° C.
  2. filtrationthe mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in 200 ml of ethanol
  5. temperature2 ml of concentrated sulfuric acid and the solution is refluxed for 22 hours
  6. customThe solvent is evaporated off
  7. additionthe residue is treated with water
  8. extractionextracted with ether
  9. customThe organic phase is separated off
  10. washwashed with water, sodium bicarbonate solution (10% by weight) and saturated sodium chloride solution
  11. customdried
  12. customevaporated
  13. distillationDistillation of the residue under high vacuum (1 mbar, 137°-141° C.)

Sources & evidence

ORD record
ord-d12b2bf5537a45e383d6e94c1b6b15df
Source dataset
uspto-grants-1989_08
Patent number
US04855084

Reaction notes

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