Hydrochloric Acid → HCID 20219312, compound

HRID 235687Notes

Reaction equation

HRID 235687 reaction equation
[C:1](Cl)(=[O: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].O1CCC[CH2:22]1.[OH2:26].Cl>C(OCC)(=O)C>[OH:26][CH2:22][C:1](=[O: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]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 8212Stearoyl chloride

Product 1

HCID 20219312HCID 20219312, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of about 96.5 g of octadecanoic acid chloride and about 205.06 g of tris-trimethylsilyloxyethylene was heated at about 110°-115° C. for about 2 hours. Another about 65 g of tris-trimethylsilyloxyethylene was added and heating was continued for about one more hour. The solution was poured slowly into a mixture of about 300 ml of tetrahydrofuran, about 300 ml of water and about 50 ml of concentrated hydrochloric acid with vigorous stirring (exothermic). The mixture was stirred at reflux for about 15 minutes and then diluted with about 1000 ml ethyl acetate. The water layer was separated from the hot mixture. The ethyl acetate layer was kept hot (about 0° C.), and saturated aqueous sodium bicarbonate was added. The resulting mixture was stirred for about 10 minutes. The organic layer was separated, dried, evaporated and recrystallized from methanol, giving about 81.3 g of the desired title compound as a white solid, mp 78°-80° C.

Workup

  1. temperaturewas heated at about 110°-115° C. for about 2 hours
  2. temperatureheating
  3. stirringThe mixture was stirred
  4. temperatureat reflux for about 15 minutes
  5. customThe water layer was separated from the hot mixture
  6. custom(about 0° C.), and saturated aqueous sodium bicarbonate
  7. additionwas added
  8. stirringThe resulting mixture was stirred for about 10 minutes
  9. customThe organic layer was separated
  10. customdried
  11. customevaporated
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9ce1a1a3bf434ee58a0f34d77d1216e4
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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