Hydrochloric Acid → Naphthalene, 1-(methoxymethoxy)-8-(1-methylethyl)-

HRID 488122Notes

Reaction equation

HRID 488122 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH:15]([CH3:17])[CH3:16])[CH:8]=[CH:7][CH:6]=1)(=[O:3])C.[CH3:18][O-].[Na+].O.Cl>CO>[CH:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:5]([O:4][CH2:1][O:3][CH3:18])=[CH:6][CH:7]=[CH:8]2)([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10443764HCID 10443764, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10105266Naphthalene, 1-(methoxymethoxy)-8-(1-methylethyl)-Yield 95.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

8.40 g of 8-isopropyl-1-naphthyl acetate was dissolved in 50 ml of methanol, to which 2.2 g of sodium methoxide was added at room temperature, followed by agitation for 10 minutes as it is. Water was added to the solution, which was rendered acidic by the use of 1N hydrochloric acid, followed by extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution and dried with anhydrous magnesium sulfate, from which the solvent was distilled off. The resulting residue was dissolved in 30 ml of dimethylformamide without purification, to which 1.94 g of 60% sodium hydride was added at room temperature. After 10 minutes, it was cooled down to 0° C., to which 5.96 g of chloromethyl methyl ether was added, followed by agitation for 15 minutes as it is. Water was added to the solution which was extracted with ethyl acetate, and th resultant organic phase was washed with a saturated saline solution and dried with anhydrous magnesium sulfate, from which the solvent was distilled off. The resultant residue was purified by silica gel column chromatography (3% ethyl acetate/hexane) to obtain 8.13 g of the captioned compound as a light yellow oily substance.

Workup

  1. additionwas added at room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant organic phase was washed with a saturated saline solution
  4. dry with materialdried with anhydrous magnesium sulfate, from which the solvent
  5. distillationwas distilled off
  6. dissolutionThe resulting residue was dissolved in 30 ml of dimethylformamide without purification, to which 1.94 g of 60% sodium hydride
  7. additionwas added at room temperature
  8. waitAfter 10 minutes
  9. additionwas added
  10. waitfollowed by agitation for 15 minutes as it
  11. additionWater was added to the solution which
  12. extractionwas extracted with ethyl acetate
  13. washth resultant organic phase was washed with a saturated saline solution
  14. dry with materialdried with anhydrous magnesium sulfate, from which the solvent
  15. distillationwas distilled off
  16. customThe resultant residue was purified by silica gel column chromatography (3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b8d307bdf0bd47fcb9279e1a69e407a6
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

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