Dihydrocoumarin → 4-(2,3-Epoxypropoxy)-1-oxoindane

HRID 1903071Notes

Reaction equation

HRID 1903071 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:2]1=[O:3].[Cl-].[Al+3].[Cl-].[Cl-].OC1C=CC=[C:22]2C=1C[CH2:20][C:21]2=[O:26].C(C1OC1)Cl.[OH-].[Na+]>>[O:26]1[CH2:22][CH:21]1[CH2:20][O:1][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:6]=1[CH2:5][CH2:4][C:2]2=[O:3]

Participants

6

Reactant 5

HCID 660DihydrocoumarinHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 5905474-Hydroxy-1-indanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 128311224-(2,3-Epoxypropoxy)-1-oxoindane

Procedure

3,4-Dihydrocumarine is allowed to react with anhydrous aluminum chloride at 200° C. and the resulting 4-hydroxyindanone is allowed to react with epichlorohydrin in an aqueous solution of sodium hydroxide to give 4-(2,3-epoxypropoxy)-1-indanone (cf. Japanese Patent No. Sho-48-817).

Sources & evidence

ORD record
ord-ee2b835f7af9431b9479a4195074c11e
Source dataset
uspto-grants-1984_03
Patent number
US04435397

Reaction notes

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