Hydrochloric Acid → HCID 19847263, compound

HRID 2350845Notes

Reaction equation

HRID 2350845 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl.[Sn](Cl)(Cl)(Cl)Cl.[C:26]1(=O)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:36])[CH:28]=[CH:27]1.[C:38](OCC)(=[O:40])[CH3:39]>>[C:38]([O:36][C:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:27][CH:28]=1)(=[O:40])[CH3:39]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8221Stearyl AlcoholHCID 85301,4-NaphthoquinoneHCID 8857Ethyl AcetateHCID 24287Tin tetrachloride

Product 1

HCID 19847263HCID 19847263, compoundYield 52%

Conditions

Temperature
60 °C

Procedure

An amount of 250 ml of octadecanol was dissolved by heating to 60° C. and 8.0 g of hydrochloric acid gas was blown thereinto little by little. Next, 44.5 g of anhydrous tin chloride and 25.0 g of 1,4-naphthoquinone were added, and the mixture was heated on a water bath of 75° C. for 2 hours. After the reaction, the product was poured into 1,000 ml of ethyl acetate, the insolubles were filtered off, and the ethyl acetate layer was washed with water. After evaporation of ethyl acetate under reduced pressure, octadecanol was recovered by vacuum distillation. The residue was dissolved in 30 ml of anhydrous acetic acid, and 2 to 3 drops of conc. sulfuric acid were added thereto, whereby vigorous heat generation occurred. After 30 minutes, ice-water was added, and the oily product separated was extracted with 500 ml of n-hexane. After washing with water and drying, the solvent ws evaporated and the residue was purified by column chromatography to obtain a thick syruppy desired product at a yield of 52%. The product was confirmed by NMR, Mass spectra.

Workup

  1. temperaturethe mixture was heated on a water bath of 75° C. for 2 hours
  2. customAfter the reaction
  3. filtrationthe insolubles were filtered off
  4. washthe ethyl acetate layer was washed with water
  5. customAfter evaporation of ethyl acetate under reduced pressure, octadecanol
  6. distillationwas recovered by vacuum distillation
  7. dissolutionThe residue was dissolved in 30 ml of anhydrous acetic acid
  8. addition2 to 3 drops of conc. sulfuric acid were added
  9. additionice-water was added
  10. customthe oily product separated
  11. extractionwas extracted with 500 ml of n-hexane
  12. washAfter washing with water
  13. customdrying
  14. customthe solvent ws evaporated
  15. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9917394f52ed4f6baf9588d94fa81d18
Source dataset
uspto-grants-1989_10
Patent number
US04871655

Reaction notes

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