Acetone → 5-Ethyl-4-hydroxy-3-methoxy-1-naphthalenecarbaldehyde

HRID 654671Notes

Reaction equation

HRID 654671 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([O:13]COC)=[C:10]([O:17][CH3:18])[CH:9]=[CH:8]2)[CH3:2].C[C:20](C)=[O:21]>Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([OH:13])=[C:10]([O:17][CH3:18])[CH:9]=[C:8]2[CH:20]=[O:21])[CH3:2]

Participants

4

Reactant 2

HCID 180AcetoneHCID 101059698-Ethyl-2-methoxy-1-methoxymethoxynaphthalene

Product 1

HCID 102632395-Ethyl-4-hydroxy-3-methoxy-1-naphthalenecarbaldehyde

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

200 g of 8-ethyl-2-methoxy-1-methoxymethoxynaphthalene was dissolved in 1 liter of acetone, to which dilute hydrochloric acid (concentrated hydrochloric acid 81 ml/water 200 ml) was added under ice-cooling conditions, after which the ice bath was removed, followed by agitation at room temperature for 5 hours. The reaction solution was poured into iced water and extracted with ethyl acetate. The resultant organic phase was washed with a saturated saline solution and dried with anhydrous magnesium sulfate. After removal of the solvent by distillation, 178 g of the resultant oily substance was dissolved in dichloromethane, to which 178 ml of titanium tetrachloride was gently added under ice-cooling conditions. After agitation for 30 minutes, 121 ml of dichloromethyl methyl ether was gradually added and agitated for 30 minutes. Iced water was gently added to the reaction solution, followed by extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution and dried with anhydrous magnesium sulfate. After removal of the solvent by distillation, the resultant residue was washed with a mixture of hexane/isopropyl ether (1:1) to obtain 110 g of the caption compound as yellowish brown crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling conditions
  3. customafter which the ice bath was removed
  4. additionThe reaction solution was poured into iced water
  5. extractionextracted with ethyl acetate
  6. washThe resultant organic phase was washed with a saturated saline solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customAfter removal of the solvent
  9. distillationby distillation, 178 g of the resultant oily substance
  10. dissolutionwas dissolved in dichloromethane, to which 178 ml of titanium tetrachloride
  11. additionwas gently added under ice-
  12. temperaturecooling conditions
  13. waitAfter agitation for 30 minutes
  14. addition121 ml of dichloromethyl methyl ether was gradually added
  15. additionIced water was gently added to the reaction solution
  16. extractionfollowed by extraction with ethyl acetate
  17. washThe resultant organic phase was washed with a saturated saline solution
  18. dry with materialdried with anhydrous magnesium sulfate
  19. customAfter removal of the solvent
  20. distillationby distillation
  21. washthe resultant residue was washed with a mixture of hexane/isopropyl ether (1:1)

Sources & evidence

ORD record
ord-113c2285f37c42d2a951f3ae49aa8ece
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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