Water → 3,4-dihydro-6,7-dimethoxy-1-isopropyl-2(1H)-naphthalenone

HRID 2118763Notes

Reaction equation

HRID 2118763 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][C:8](=[O:15])[CH2:7][CH2:6]2.[CH:16](I)([CH3:18])[CH3:17].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH:16]([CH3:18])[CH3:17])[C:8](=[O:15])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 6362Isopropyl iodideHCID 6098446,7-Dimethoxy-2-tetralone

Product 1

HCID 201932173,4-dihydro-6,7-dimethoxy-1-isopropyl-2(1H)-naphthalenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.0 g of 3,4-dihydro-6,7-dimethoxy-2(1H)-naphthalenone were dissolved in 300 ml of dimethylformamide and treated with 13 g of potassium tert.-butylate. The solution was stirred at 18° for 30 minutes. After the addition of 19.7 g of isopropyl iodide the mixture was stirred for a further 30 minutes, whereby the temperature was held below 30°, and then poured into water. The product was extracted with ether, the extract was washed with water, dried over magnesium sulfate and evaporated. The oil which remained behind was purified by column chromatography (silica gel, hexane/ethyl acetate 6:1). There was obtained 3,4-dihydro-6,7-dimethoxy-1-isopropyl-2(1H)-naphthalenone, m.p. 77°-79°.

Workup

  1. stirringwas stirred for a further 30 minutes
  2. customwas held below 30°
  3. extractionThe product was extracted with ether
  4. washthe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. custombehind was purified by column chromatography (silica gel, hexane/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-f1ff44d08042418d8a29d8756096b2f6
Source dataset
uspto-grants-1987_07
Patent number
US04680310

Reaction notes

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