Ethyl Acetate → 2,3-Epoxy-1,2,3,4-tetrahydronaphthalene

HRID 2286755Notes

Reaction equation

HRID 2286755 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](OO)=O)[CH:3]=1.C1C2CC=CCC=2C=CC=1.[C:22]([O:25][CH2:26][CH3:27])(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)C>[O:25]1[CH:26]2[CH:22]1[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[CH2:27]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 691551,4-DihydronaphthaleneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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.

Workup

  1. custom##STR6## The reaction
  2. additionmixed

Sources & evidence

ORD record
ord-940e381742b3408ca2839f1a83bb32fe
Source dataset
uspto-grants-1981_05
Patent number
US04267373

Reaction notes

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