Hydrochloric Acid → Isopropyl 7,11dimethyl-3-oxo-6,10-dodecadienoate

HRID 436875Notes

Reaction equation

HRID 436875 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:5][CH2:6][CH2:7][C:8](=[O:14])[CH2:9][C:10](OC)=[O:11].O.Cl.[CH:23]([OH:26])([CH3:25])[CH3:24]>>[CH3:3][C:4]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:5][CH2:6][CH2:7][C:8](=[O:14])[CH2:9][C:10]([O:26][CH:23]([CH3:25])[CH3:24])=[O:11]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3776Isopropanol3×HCID 24758Sodium hydrideHCID 53708905HCID 53708905, compound

Product 1

HCID 54226106Isopropyl 7,11dimethyl-3-oxo-6,10-dodecadienoate

Procedure

A solution of 1.92 g of sodium hydride in 200 ml of isopropanol was added to a boiling mixture of 10 g of the product of Example 3 and 200 ml of isopropanol and the volume was held constant by replacing proportionately the distillate with isopropanol for 2 hours. After cooling, the mixture was poured into water and acidified with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate and the extract was washed with water, dried over sodium sulfate and evaporated to dryness. The residue was chromatographed over silica and was eluted with a 9-1 petroleum ether (b.p.= 40°-75° C.)-ethyl ether mixture to obtain 7.05 g of isopropyl 7,11dimethyl-3-oxo-6,10-dodecadienoate in the form of an amber oil with a refractive index of nD24 = 1.467.

Workup

  1. customfor 2 hours
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was chromatographed over silica
  8. washwas eluted with a 9-1 petroleum ether (b.p.= 40°-75° C.)-ethyl ether mixture

Sources & evidence

ORD record
ord-cf8458b1f1734c778fa9defa19dc2a9e
Source dataset
uspto-grants-1977_06
Patent number
US04028386

Reaction notes

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