Succinic anhydride → HCID 14234808, compound

HRID 1607129Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1.[Cl-].[Al+3].[Cl-].[Cl-]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

Reactant 3

HCID 7922Succinic anhydride

HCID 10329Dihydrobenzofuran

HCID 6451240Aluminum(III) Chloride

Product 1

HCID 14234808HCID 14234808, compound

Procedure

2,3-dihydrobenzofuran of formula II, ##STR5## is condensed with succinic anhydride in the presence of aluminum chloride in a chlorinated organic solvent and at a temperature below 5° C., to form 4-(2,3-dihydro-5-benzofuranyl)-4-oxobutanoic acid of formula III, ##STR6## which is reduced in acid medium in the heated state and in the presence of zinc and mercuric chloride to form 4-(2,3-dihydro-5-benzofuranyl)butanoic acid of formula IV, ##STR7## which is then subjected to the action of polyphosphoric acid in an apolar organic solvent and at a temperature of between 80° C. and 100° C. to form 2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-8-one of formula V, ##STR8## which is then:

Sources & evidence

ORD record: ord-e8aec51b8ba04acdaa1ae792f6f1f7d0
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863951

Reaction notes

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