5,6,7,8-Tetrahydronaphthalene-1,6-diol → 2-Naphthol

Participants

Reaction Steps

Employing the procedure of Example 3 (a), but substituting a 6-alkoxy-1-tetralone as shown in the left hand (first) column of Table II for 6-methoxy-1-tetralone, a 6-alkoxy-1-naphthol is produced, which is converted as per Example 3 (b) to the corresponding 5-hydroxy-3,4-dihydro-2(1 H)-naphthalenenone shown in the middle column of Table II; employing the procedure of Example 3 (c) the naphthalenone is converted to the corresponding 5,6,7,8-tetrahydro-1,6-naphthalenediol which is reacted with an epoxide of the structure ##EQU13## in accordance with the procedure of Example 3 d to form the corresponding 1,2,3,4-tetrahydro-5-[2,3-epoxy-propoxy]-2-naphthol which is reacted with an amine of the structure ##EQU14## in accordance with the procedure of Example 3 e to form the corresponding 1,2,3,4-tetrahydro-5-[2-hydroxy-3-(R1, R2 -substituted amino)propoxy]-2-naphthol (formula I) as shown in the right hand (third) column of Table II.

Provenance & Evidence