Hydrochloric Acid → HCID 178442844, compound

HRID 974693Notes

Reaction equation

HRID 974693 reaction equation
Cl.[NH2:2]O.[OH-].[Na+].C1CO[C:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH2:9][C:10](OCC)=[O:11])[O:7]1.Cl>O.C(O)C>[OH:11][C:10]1[CH:9]=[C:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[O:7][N:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19986110HCID 19986110, compound

Product 1

HCID 178442844HCID 178442844, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

11.12 g of hydroxylamine hydrochloride were added to a solution of 12.60 g of sodium hydroxide in a mixture of 80 ml of water and 100 ml of ethanol, whilst ice-cooling. A solution of the whole of the crude ethyl 3,3-ethylenedioxystearate prepared as described above in 200 ml of ethanol was added all at once, whilst ice-cooling, to the resulting mixture. The reaction mixture was then stirred at room temperature for 2 hours. At the end of this time, 100 ml of concentrated hydrochloric acid were added, and the mixture was heated under reflux for 1.5 hours. The mixture was allowed to cool, and the precipitated solid was collected by filtration and dissolved in methylene chloride. The methylene chloride solution was washed with a saturated aqueous solution of sodium bicarbonate and with water, dried and concentrated by evaporation under reduced pressure. The residue was filtered with the aid of suction to give 7.19 g of the title compound as crystals. An oily material (19 g) separated from the filtration was subjected to column chromatography through 250 g of alumina (grade III). From the fractions eluted with a 20:1 by volume mixture of methanol and acetic acid, an additional 0.82 g of crystals was obtained. These crystals melted at 81.5°-82.5° C. (from cold methylene chloride).

Workup

  1. temperaturecooling
  2. additionwas added all at once, whilst ice-
  3. temperaturecooling, to the resulting mixture
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 1.5 hours
  6. temperatureto cool
  7. filtrationthe precipitated solid was collected by filtration
  8. dissolutiondissolved in methylene chloride
  9. washThe methylene chloride solution was washed with a saturated aqueous solution of sodium bicarbonate and with water
  10. customdried
  11. concentrationconcentrated by evaporation under reduced pressure
  12. filtrationThe residue was filtered with the aid of suction

Sources & evidence

ORD record
ord-3213c249e7e54c97b7a076781ba8606f
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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