1,4-Dihydronaphthalene → 2,3-Epoxy-1,2,3,4-tetrahydronaphthalene

HRID 2286754Notes

Reaction equation

HRID 2286754 reaction equation
[CH:1]1[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>>[O:19]1[CH:8]2[CH:7]1[CH2:6][C:5]1[CH:4]=[CH:3][CH:2]=[CH:1][C:10]=1[CH2:9]2

Participants

3

Reactant 2

HCID 691551,4-DihydronaphthaleneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 108880512,3-Epoxy-1,2,3,4-tetrahydronaphthalene

Procedure

Reaction of a 5,8-dihydronaphthalene of formula III or formula IV with m-chloroperbenzoic acid yields a 5,6,7,8-tetrahydro-6,7-epoxynaphthalene having the structure ##STR6## The reaction can be carried out by mixing m-chloroperbenzoic acid with a solution of a 5,8-dihydronaphthalene in an organic solvent, e.g., ethyl acetate. The resulting mixture is added to a mixture of ethyl ether and aqueous sodium bicarbonate, and mixed to form a 5,6,7,8-tetrahydro-6,7-epoxynaphthalene of formula V.

Sources & evidence

ORD record
ord-04585a0685a34251bb45af99926871de
Source dataset
uspto-grants-1981_05
Patent number
US04267373

Reaction notes

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