Sodium Iodide → HCID 11313625, compound

HRID 430861Notes

Reaction equation

HRID 430861 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(=O)O[CH2:19][CH2:18][O:17]1.[I-].[Na+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:24]([O:17][CH2:18][CH2:19][O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 7303Ethylene carbonateHCID 7503Benzyl ChlorideHCID 7638MonobenzoneHCID 14798Sodium Hydroxide

Product 1

HCID 11313625HCID 11313625, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
155 °C

Procedure

4-Benzyloxyphenol (60.6 g, 0.3 mole), ethylene carbonate (32.0 g, 0.36 mole) and sodium iodide (2.25 g, 0.015 mole) were placed in a 500 ml, three-necked, round-bottom flask equipped with a mechanical stirrer and a reflux condenser. The reaction mixture was stirred and heated at 155° C. After 5 hours, the reaction mixture was cooled to 110° C. and most of the lower boiling materials were removed under reduced pressure. Then, tetrabutylammonium hydrogen sulfate (4.0 g, 0.12 mole), benzyl chloride (45.0 g, 0.35 mole), toluene (200 ml) and sodium hydroxide (20.0 g, 0.5 mole/40 ml of water) were added to the reaction mixture and the vigorous stirring was continued while the reaction mixture temperature was lowered to 90° C. After overnight at this temperature, the reaction mixture was cooled to room temperature and transferred to a separatory funnel. The toluene layer was separated and the aqueous layer was extracted twice with toluene. Toluene extracts were combined, washed with water, dried, treated with Norit A and filtered. The filtrated was passed through a short column of silica gel and eluted with toluene. Fractions containing the product were collected, combined and concentrated. The residue was recrystallized from methanol. Yield: 72.6 g (72%), White solid, M.P.: 71-73° C.

Workup

  1. customthree-necked, round-bottom flask equipped with a mechanical stirrer and a reflux condenser
  2. temperaturethe reaction mixture was cooled to 110° C. and most of the lower boiling materials
  3. customwere removed under reduced pressure
  4. stirringthe vigorous stirring
  5. customwas lowered to 90° C
  6. waitAfter overnight at this temperature
  7. temperaturethe reaction mixture was cooled to room temperature
  8. customtransferred to a separatory funnel
  9. customThe toluene layer was separated
  10. extractionthe aqueous layer was extracted twice with toluene
  11. washwashed with water
  12. customdried
  13. additiontreated with Norit A and
  14. filtrationfiltered
  15. washeluted with toluene
  16. additionFractions containing the product
  17. customwere collected
  18. concentrationconcentrated
  19. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-066917e6ea0a4f28ae90463a14c2828f
Source dataset
uspto-grants-2001_11
Patent number
US06323376B1

Reaction notes

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