2,7-Dimethoxynaphthalene → 7-Methoxy-2-tetralone
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:13]C)=[CH:8][CH:9]=2)[CH:4]=1.[Na]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10]([CH2:9][CH2:8][C:7](=[O:13])[CH2:6]2)=[CH:11][CH:12]=1Participants
Procedure
2,7-dimethoxynaphthalene of formula XXV, ##STR36## is subjected to the action of sodium metal, in the heated state and in the presence of an anhydrous alcohol, to form 7-methoxy-1,2,3,4-tetrahydro-2-naphthalenone of formula XXVI, ##STR37## which is then reacted in the heated state in an alcoholic solvent with a hydroxylamine salt to form 7-methoxy-1,2,-3,4-tetrahydro-2-naphthalenone oxime of formula XXVII, ##STR38## which is then subjected to a catalytic hydrogenation, in solution in an alcohol, in the presence of Raney nickel and ammonia, to form 2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene of formula XXVIII, ##STR39## which is condensed with acetic anhydride in acetic acid medium to form 2-acetamido-7-methoxy-1,2,3,4-tetrahydronaphthalene of formula XXIX, ##STR40## which is subjected to the action of boron tribromide, at room temperature in a halogenated organic solvent, to form 2-acetamido-7-hydroxy-1,2,3,4-tetrahydronaphthalene of formula XXX, ##STR41## which is then reacted with chloroacetonitrile, in the presence of boron trichloride and aluminum chloride, to form 2-acetamido-6-(2-chloro-1-oxoethyl)-7-hydroxy-1,2,3,4-tetrahydronaphthalene of formula XXXI, ##STR42## which is subjected to the action of triethylamine, in the heated state in a halogenated organic solvent, to form 7-acetamido-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-one of formula XXXII, ##STR43## which is then either
Sources & evidence
- ORD record
- ord-a15d225e383f4d2f8cf50ea502096394
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04885373
Reaction notes
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