2(5H)-Furanone → Biphenyl

HRID 1744897Notes

Reaction equation

HRID 1744897 reaction equation
O[C:2]1[C:3](=O)O[CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]=1O.O[C:16]1C(=O)OC(C2C=CC(Cl)=CC=2)[C:20]=1O.OC1C(=O)OC(C(O)CO)C=1O.OC1C(=O)OC(C2C=CC(C)=CC=2CCC)C=1O.O1CC=CC1=O>>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:20]=[CH:16][CH:3]=[CH:2][CH:6]=1

Participants

6

Reactant 5

HCID 103412(5H)-FuranoneHCID 546766344-Phenyl-2,3-dihydroxy-2-buten-4-olideHCID 54676860D-erythro-hex-2-enonic acid, gamma-lactoneHCID 547112284-(4-Chlorophenyl)-2-hydroxytetronic acidHCID 865859713,4-dihydroxy-5-(4'methylpropylphenyl)-2(5H)-furanone

Product 1

HCID 7095Biphenyl

Procedure

Non-limiting examples of known compounds useful for the present invention wherein one R (R1) is H and the other (R2) is a substituted or unsubstituted phenyl group include 3,4-dihydroxy-5-phenyl-2(5H)-furanone (sometimes called 4-phenyl-2-hydroxytetronic acid); 3,4-dihydroxy-5-(4′-chlorophenyl)-2(5H)-furanone (sometimes called 4-(4′-chlorophenyl)-2-hydroxytetronic acid); 3,4-dihydroxy-5-(1′,2′-dihydroxyethyl)-2(5H)-furanone (sometimes called 4-dihydroxyethyl-2-hydroxytetronic acid); 3,4-dihydroxy-5-(4′methylpropylphenyl)-2(5H)-furanone; and 3,4-dihydroxy-5-[4-(5-methylfur)-2-yl)phenyl]-2(5H)-furanone. As mentioned above, a subgroup bearing these substituents include compounds wherein R1 is H and R2 is a phenyl bearing another phenyl, forming a biphenyl, such as 3,4-dihydroxy-5-(1,1′-biphenyl)-2(5H)-furanone (sometimes called 4-biphenyl-2-hydroxytetronic acid); 3,4-dihydroxy-5-(4″-chlorobiphenyl)-2(5H)-furanone (sometimes called 4-chloro-biphe-nyl)-2-hydroxytetronic acid); 3,4-dihydroxy-5-[(4′-nitro-1,1′-biphenyl)-4-yl]-2(5H)-furanone; 3,4-dihydroxy-5-[(4′-methyl-1,1′-biphenyl)-4-yl]-2(5H)-furanone; 3,4-dihydroxy-5-[(2′,4′-dimethyl-1,1′-biphenyl)-4-yl]-2(5H)-furanone; 3,4-dihydroxy-5-[(3′,4′-dimethyl-1,1′-biphenyl)-4-yl]-2(5H)-furanone; and 3,4-dihydroxy-5-[(4′-meth-oxy-1,1′-biphenyl)-4-yl]-2(5H)-furanone. In another subgroup of compounds, R1 is H and R2 is a phenyl substituted with a heteroaromatic (furyl or pyridyl) group such as, for example, 3,4-dihydroxy-5-[4-(5-methylfur)-2-yl)phenyl]-2(5H)-furanone; 3,4-dihydroxy-5-[4-(5-methylpyrid)-2-yl)phenyl]-2(5H)-furanone; 3,4-dihydroxy-5-[4-(3-methylpyrid)-2-yl)phenyl]-2(5H)-furanone; 3,4-dihydroxy-5-[4-(4-methylpyrid)-2-yl)phenyl]-2(5H)-furanone; 3,4-dihydroxy-5-[4-(4-methylpyrid)-3-yl)phenyl]-2(5H)-furanone; 3,4-dihydroxy-5-[4-(5-methylpyrid)-3-yl)phenyl]-2(5H)-furanone; and 3,4-dihydroxy-5-[4-(2-methylpyrid)-3-yl)phenyl]-2(5H)-furanone.

Sources & evidence

ORD record
ord-0650d3756b814872a3cddb084a0729bc
Source dataset
uspto-grants-2006_03
Patent number
US07019029B2

Reaction notes

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