Chloroform → 3,6-Dioxatricyclo[5.4.0.0,2,4]undeca-1(11),7,9-triene

HRID 862477Notes

Reaction equation

HRID 862477 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:19])C=1.C(OO)(=O)C.C(Cl)(Cl)Cl>CCOCC.C(Cl)Cl>[O:19]1[CH:4]2[CH:3]1[CH2:2][O:1][C:10]1[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6585Peracetic AcidHCID 9211BenzopyranHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 131490333,6-Dioxatricyclo[5.4.0.0,2,4]undeca-1(11),7,9-triene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The compound 5 is oxidized with an oxidizing agent such as m-chloroperbenzoic acid and peracetic acid in a solvent such as chloroform, methylene chloride and ether, under cooling to room temperature to give 3,4-epoxychroman (compound 6 wherein R1, R2 and R3 are as defined above).

Sources & evidence

ORD record
ord-90bec408a66c447abc6e93e4705880ed
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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