3a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dione → 3-Cyclohexene-1,2-dicarboxylic acid

HRID 1577041Notes

Reaction equation

HRID 1577041 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH:4][CH2:5][CH2:6][CH:7]([OH:9])[CH3:8].[C:10]1(=[O:20])[O:15][C:13](=[O:14])[CH:12]2[CH2:16][CH2:17][CH:18]=[CH:19][CH:11]12>C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C1(C)C(C)=CC=CC=1>[CH2:1]=[CH:2][CH:3]=[CH:4][CH2:5][CH2:6][CH:7]([OH:9])[CH3:8].[C:10]([OH:15])(=[O:20])[CH:11]1[CH:19]=[CH:18][CH2:17][CH2:16][CH:12]1[C:13]([OH:9])=[O:14]

Participants

6

Reactant 2

HCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dioneHCID 572477947-Octadienol

Product 2

HCID 127266073-Cyclohexene-1,2-dicarboxylic acidHCID 572477947-Octadienol

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalyst2×HCID 7237O-XyleneSolvent

Procedure

In a 1 liter glass autoclave equipped with a thermometer, a condenser, a nitrogen gas inlet and a stirrer, 378 g. (3.0 mole) of 2, 7 - octadienol - 1, 152 g. (1.0 mole) of tetrahydrophthalic anhydride, 100 ml. of xylene and 0.5g. of zinc acetate 2 - hydrate were charged. In accordance with the process of Reference Example 1, 388 g of the di-(2, 7 - octadienol - 1) ester of tetrahydrophthalic acid was obtained as the product.

Sources & evidence

ORD record
ord-53e235e243144e55bbdb0b8b0b7d28ac
Source dataset
uspto-grants-1976_09
Patent number
US03983289

Reaction notes

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