4-hydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-3-phenylmethoxy-2(5H)-furanone → 3,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone

HRID 369140Notes

Reaction equation

HRID 369140 reaction equation
[OH:1][C:2]1[C:6]([CH3:17])([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=2)[O:5][C:4](=[O:18])[C:3]=1[O:19]CC1C=CC=CC=1.OC1C(=O)OC(C)(C2C=CC=CC=2)C=1O>>[OH:19][C:3]1[C:4](=[O:18])[O:5][C:6]([CH3:17])([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:11][CH:12]=2)[C:2]=1[OH:1]

Participants

3

Reactant 2

HCID 547236014-hydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-3-phenylmethoxy-2(5H)-furanoneHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

Product 1

HCID 547254983,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanoneYield 84%

Procedure

Hydrogenolysis of 800 mg (2.3 mmol) of 4-hydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-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 500 mg (84% yield) of 3,4-dihydroxy-5-methyl-5-[4-(2-methylpropyl)phenyl]-2(5H)-furanone as a light yellow crystalline material: mp 135-150° C. dec. 1H NMR (acetone-d6) δ 7.40-7.17 (m, 4H), 2.46 (d, 2H, J=7.1 Hz), 1.87-1.82 (m, 1H), 1.82 (s, 3H), 0.87 (d, 6H, J=6.6 Hz). 13C NMR (acetone-d6) δ 169.5, 157.2, 142.4, 138.0, 129.8, 125.9, 117.9, 81.3, 45.3, 30.8, 24.5, 22.5. Anal Calcd for C15H18O4 +0.25 H2O: C, 67.53; H, 6.99. Found: C, 67.78; H, 7.09.

Sources & evidence

ORD record
ord-0c2859c6cd744daf8f890a7ffc869141
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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