Benzyl Chloride → 4-(Benzyloxy)naphthalen-1-ol

HRID 2247845Notes

Reaction equation

HRID 2247845 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[K+].[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH2:23]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 113051,4-NaphthalenediolHCID 14797Potassium HydroxideHCID 24489Sodium Dithionite

Product 1

HCID 5629374-(Benzyloxy)naphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

23.7 g. (0.147 mole) 1,4-Dihydroxynaphthalene (purified by shaking an ethereal solution thereof with sodium dithionite solution) are dissolved in 200 ml. acetone. After adding 20.3 g. (0.147 mole) of pulverised potassium hydroxide and heating to reflux temperature, 18.6 g. (16.9 ml.) benzyl chloride are added dropwise thereto in the course of 60 minutes. The reaction mixture is thereafter heated under reflux for 4 hours while stirring, evaporated and the residue is mixed with 100 ml. water and extracted with diethyl ether. The ethereal solution is dried with anhydrous magnesium sulphate, filtered and evaporated. The tar-like residue is extracted with cyclohexane. The combined extracts are cooled, considerable amounts of a tarry product thereby first separating out. Thereafter, the pure compound crystallises out. It is washed with cyclohexane and dried. Yield 4.3 g. (11.9% of theory); m.p. 118°-119° C.

Workup

  1. additionAfter adding 20.3 g
  2. temperatureto reflux temperature, 18.6 g
  3. customin the course of 60 minutes
  4. temperatureThe reaction mixture is thereafter heated
  5. temperatureunder reflux for 4 hours
  6. stirringwhile stirring
  7. customevaporated
  8. additionthe residue is mixed with 100 ml
  9. extractionwater and extracted with diethyl ether
  10. dry with materialThe ethereal solution is dried with anhydrous magnesium sulphate
  11. filtrationfiltered
  12. customevaporated
  13. extractionThe tar-like residue is extracted with cyclohexane
  14. temperatureThe combined extracts are cooled
  15. customconsiderable amounts of a tarry product thereby first separating out
  16. customThereafter, the pure compound crystallises out
  17. washIt is washed with cyclohexane
  18. customdried

Sources & evidence

ORD record
ord-3dbb469d4090486a9073712ff1576cff
Source dataset
uspto-grants-1991_08
Patent number
US05037828

Reaction notes

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