Benzyl Chloride → HCID 13037174, compound

HRID 1759253Notes

Reaction equation

HRID 1759253 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:2]([OH:1])=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 77548Ethyl 2,5-dihydroxybenzoate

Product 1

HCID 13037174HCID 13037174, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 100 ml of acetone is dissolved 15 g (0.0824 moles) of ethyl 2,5-dihydroxybenzoate, 13.9 g (0.110 mole) benzyl chloride and 34.1 g (0.247 mole) potassium carbonate. The mixture is heated to its reflux temperature and maintained at reflux for 22 hours. The solution is filtered and the residue is washed with acetone. The filtrate and washings are concentrated, and the residue is dissolved in diethyl ether. The ether extracts are washed twice with water then with saturated sodium chloride solution and finally dried over magnesium sulfate. The magnesium sulfate is removed by filtration and the solution is evaporated to provide a suspension of product which is triturated with hexane and dried to provide a solid. The solid is recrystallized from hexane to provide ethyl 5-benzyloxy-2-hydroxybenzoate, m.p. 71.5°-73° C.

Workup

  1. temperatureThe mixture is heated to its
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for 22 hours
  5. filtrationThe solution is filtered
  6. washthe residue is washed with acetone
  7. concentrationThe filtrate and washings are concentrated
  8. dissolutionthe residue is dissolved in diethyl ether
  9. washThe ether extracts are washed twice with water
  10. dry with materialwith saturated sodium chloride solution and finally dried over magnesium sulfate
  11. customThe magnesium sulfate is removed by filtration
  12. customthe solution is evaporated
  13. customto provide
  14. additiona suspension of product which
  15. customis triturated with hexane
  16. customdried
  17. customto provide a solid
  18. customThe solid is recrystallized from hexane

Sources & evidence

ORD record
ord-92f211cf81ae4eeaaa1ff8ce7ace554c
Source dataset
uspto-grants-1982_07
Patent number
US04339587

Reaction notes

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