Perchloric Acid → trans-5,6,7,8-Tetrahydro-1,6,7-naphthalenetriol

HRID 263316

Reaction equation

HRID 263316 reaction equation
[O:1]1[CH:11]2[CH:2]1[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:12])[C:9]=1[CH2:10]2.Cl(O)(=O)(=O)=[O:14]>O1CCCC1>[C:8]1([OH:12])[C:9]2[CH2:10][C@@H:11]([OH:1])[C@H:2]([OH:14])[CH2:3][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 124457371a,2,7,7a-Tetrahydronaphtho[2,3-b]oxiren-3-ol

Product 1

HCID 12445740trans-5,6,7,8-Tetrahydro-1,6,7-naphthalenetriol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, the 2,3-trans-1,2,3,4-tetrahydro-5-[2-hydroxy-3-(substituted-amino)propoxy]-2,3-naphthalenediol isomer XXVII can be prepared from a 5,8-dihydro-1-naphthol of the structure ##STR34## prepared as described hereinbefore, by mixing a cooled solution (temperature less than about 30° C.) of 5,8-dihydro-1-naphthol in ethyl acetate with m-chloroperbenzoic acid and mixing the resulting slurry with a mixture of ethyl ether and aqueous sodium bicarbonate, to form 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol ##STR35## and reacting the 5,6,7,8-tetrahydro-6,7-epoxy-1-naphthol in tetrahydrofuran with aqueous perchloric acid at a temperature within the range of from about 0° to about 60° C., to form trans-5,6,7,8-tetrahydro-1,6,7-naphthalenetriol XXV which can be converted to the 2,3-trans-1,2,3,4-tetrahydro-5-[2,3-(epoxy)-propoxy]-2,3-naphthalenediol XXVI which in turn can be converted to the 2,3-trans-1,2,3,4-tetrahydro-5-[2-hydroxy-3-substituted amino)propoxy]-2,3-naphthalenediol XXVII in a manner similar to that described hereinbefore.

Workup

  1. customof from about 0° to about 60° C.

Sources & evidence

ORD record
ord-83551eb664a44a439fce98884c76c14b
Source dataset
uspto-grants-1979_05
Patent number
US04156789

Linked notes

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