Hydrochloric Acid → HCID 19022304, compound

HRID 1109319Notes

Reaction equation

HRID 1109319 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([O:18]COC)=[C:15]([O:22][CH3:23])[CH:14]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>CC(C)=O>[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([OH:18])=[C:15]([O:22][CH3:23])[CH:14]=[CH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 19022386HCID 19022386, compound

Product 1

HCID 19022304HCID 19022304, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

79.5 g of 8-benzyl-2-methoxy-1-methoxymethoxynaphthalene was dissolved in 300 ml of acetone to give a solution. 120 ml of 6N hydrochloric acid was added to the solution at room temperature. The obtained mixture was stirred for 1.5 hours, followed by the addition of 400 ml of water. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and distilled in a vacuum to remove the solvent. The obtained solid was washed with hexane/diisopropyl ether (1:1) to give 51 g of the title compound as a colorless crystal.

Workup

  1. customto give a solution
  2. extractionThe obtained mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled in a vacuum
  6. customto remove the solvent
  7. washThe obtained solid was washed with hexane/diisopropyl ether (1:1)

Sources & evidence

ORD record
ord-9355fab0a0164c84974edb44e70d648c
Source dataset
uspto-grants-1994_06
Patent number
US05319139

Reaction notes

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