Sodium Chloride → HCID 11313625, compound

HRID 430860Notes

Reaction equation

HRID 430860 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.[Cl-].[Na+].[OH-].[K+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[CH2:26]([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:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 7303Ethylene carbonateHCID 7503Benzyl ChlorideHCID 7638MonobenzoneHCID 14797Potassium Hydroxide

Product 1

HCID 11313625HCID 11313625, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
155 °C

Procedure

4-Benzyloxyphenol (60.6 g, 0.3 mole), ethylene carbonate (32.0 g, 0.36 mole) and sodium chloride (4.0 g, 0.07 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 to 155° C. After 9 hours, the reaction mixture was cooled to 100° C. and most of the lower boiling materials were removed under reduced pressure. Then, tetrabutylammonium hydrogen sulfate (4.0 g, 0.012 mole) and finely powdered potassium hydroxide (28.0 g, 0.5 mole) were added to the reaction mixture and the vigorous stirring was continued. After five minutes, benzyl chloride (45.0 g, 0.36 mole) was added slowly with vigorous stirring. After four hours, toluene (200 ml) and water (60 ml) were added and stirring was continued for another ten minutes. The toluene layer was separated and the aqueous layer was extracted twice with toluene. The in toluene layers were combined and washed with water, dried and concentrated. The residue was recrystallized from methanol. Yield: 82.6 g (82%), 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 100° C. and most of the lower boiling materials
  3. customwere removed under reduced pressure
  4. stirringthe vigorous stirring
  5. waitAfter five minutes
  6. waitAfter four hours
  7. stirringstirring
  8. waitwas continued for another ten minutes
  9. customThe toluene layer was separated
  10. extractionthe aqueous layer was extracted twice with toluene
  11. washwashed with water
  12. customdried
  13. concentrationconcentrated
  14. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-af8b252004e540b8abf259995479fd8d
Source dataset
uspto-grants-2001_11
Patent number
US06323376B1

Reaction notes

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