Acetone → Naphthalene, 1,7-dimethoxy- (8CI)(9CI)

HRID 2210007Notes

Reaction equation

HRID 2210007 reaction equation
[CH3:1]C(C)=O.[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13](O)[CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>O>[CH3:1][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:20][CH3:17])[CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 684621,7-Naphthalenediol

Product 1

HCID 79197Naphthalene, 1,7-dimethoxy- (8CI)(9CI)Yield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To one liter of acetone were added 50.0 grams (0.31 mole) of 1,7-dihydroxynaphthalene. To the solution then were added 95.0 gm (0.69 mole) of powdered potassium carbonate and 65 mL (0.69 mole) of dimethyl sulfate. The reaction mixture was stirred at reflux under nitrogen for 18 hours. The reaction mixture then was cooled to room temperature and diluted with 2 L of water. The mixture was then extracted with dichloromethane. The organic extracts were combined, washed successively with water and saturated aqueous sodium chloride, dried over sodium sulfate and evaporated in vacuo to give a brown oil. The oil was distilled in vacuo to give 52.51 gm (90.1%) of 1,7-dimethoxynaphthalene as a light orange, transparent oil, b.p.=115°-157° C. (4 mm Hg).

Workup

  1. temperatureat reflux under nitrogen for 18 hours
  2. extractionThe mixture was then extracted with dichloromethane
  3. washwashed successively with water and saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give a brown oil
  7. distillationThe oil was distilled in vacuo

Sources & evidence

ORD record
ord-5ec567e58200403e9f4ce1f80befb2f5
Source dataset
uspto-grants-1995_10
Patent number
US05457121

Reaction notes

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