Ethanol → 3-Ethoxy-7-methoxy-1,2-dihydronaphthalene

HRID 53972Notes

Reaction equation

HRID 53972 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.C([O-])([O-])OCC.[CH2:20]([OH:22])[CH3:21]>S(=O)(=O)(O)O>[CH2:20]([O:22][C:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)[CH3:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 53630039Ethylorthoformate

Product 1

HCID 218442353-Ethoxy-7-methoxy-1,2-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
100 °C

Procedure

33.5 g of 6-methoxy-2-tetralone was dissolved in 27.6 ml of ethanol, followed by subsequently adding 37.8 ml of ethyl orthoformate and one drop of concentrated sulfuric acid. The mixture2thus prepared was stirred at 100° C. for 4 hours. After distilling off the solvent under a reduced pressure, the resulting residue was subjected to silica gel column chromatography using chloroform as an eluant. Fractions of interest were pooled and concentrated to collect precipitated crystals, thereby obtaining 5.82 g of 3,4-dihydro-2-ethoxy-6-methoxynaphthalene.

Workup

  1. customThe mixture2thus prepared
  2. distillationAfter distilling off the solvent under a reduced pressure
  3. concentrationconcentrated
  4. customto collect
  5. customprecipitated crystals

Sources & evidence

ORD record
ord-7a4e08dd84454fa79158970f9d71be34
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Reaction notes

Loading…