5,6,7,8-Tetrahydronaphthalene-1,6-diol → 2-Naphthol
Reaction equation
C1(=O)C2C(=CC=CC=2)C=CC1.[C:12]1(O)[C:21]2[CH2:20][CH2:19][CH:18]([OH:22])[CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.O1CC1COC1C=CC=C2C=1CCC(O)C2>>[CH:17]1[C:16]2[C:21](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:20]=[CH:19][C:18]=1[OH:22]Participants
Procedure
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.
Workup
- customwith the procedure of Example 3 d
Sources & evidence
- ORD record
- ord-45629bee273c40ffa94b456f6a99b901
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03982021
Reaction notes
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