5-(4-chlorophenyl)-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanone → 5-(4-chlorophenyl)-3,4-dihydroxy-5-methyl-2(5H)-furanone

HRID 369142Notes

Reaction equation

HRID 369142 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:23])[O:12][C:11](=[O:13])[C:10]([O:14]CC3C=CC=CC=3)=[C:9]2[OH:22])=[CH:4][CH:3]=1.OC1C(=O)OC(C)(C2C=CC=CC=2)C=1O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH3:23])[O:12][C:11](=[O:13])[C:10]([OH:14])=[C:9]2[OH:22])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 547235885-(4-chlorophenyl)-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanoneHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

Product 1

HCID 547185905-(4-chlorophenyl)-3,4-dihydroxy-5-methyl-2(5H)-furanoneYield 46%

Procedure

Hydrogenolysis of 330 mg of 5-(4-chlorophenyl)-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanone was performed in a similar manner as described in the preparation of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to provided 110 mg (46% yield) of 5-(4-chlorophenyl)-3,4-dihydroxy-5-methyl-2(5H)-furanone a light tan solid: mp 154-155° C. dec.(benzene/hexanes) 1H NMR (acetone-d6) δ 7.52-7.34 (m, 4H), 1.82 (s, 3H). 13C NMR (acetone-d6) δ 169.0, 156.6, 139.8, 134.3, 129.2, 127.8, 117.9, 80.8, 24.6. Anal Calcd for C11H9ClO4 : C, 54.90; H, 3.77. Found: C, 54.74; H, 4.08.

Sources & evidence

ORD record
ord-320bacb482cc4f8a8d74824b9fb323e7
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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