4-Hydroxy-4-[3,4-dimethoxy-2-(1-methylethyl)phenyl]-3-methylbut-2-enoic Acid → 4-[3,4-Dimethoxy-2-(1-methylethyl)phenyl]-3-methylbutanoic Acid
Reaction equation
O[CH:2]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[C:10]=1[CH:19]([CH3:21])[CH3:20])[C:3]([CH3:8])=[CH:4][C:5]([OH:7])=[O:6].[H][H]>C(O)(=O)C.[Pd]>[CH3:18][O:17][C:11]1[C:10]([CH:19]([CH3:21])[CH3:20])=[C:9]([CH2:2][CH:3]([CH3:8])[CH2:4][C:5]([OH:7])=[O:6])[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Compound 9 (7.00 g, 23.8 mmol) in 100 mL of acetic acid was hydrogenated on a Parr hydrogenator with 0.4 g of 10% palladium on carbon and 60 psi hydrogen pressure at 60° C. for 20 h. The reaction mixture was vacuum filtered through celite and the celite was washed with ether. The solvent was evaporated in a fume hood and the residual oil was distilled bulb to bulb (170° C./1 torr) to give 5.95 g (21.2 mmol, 89%) of 10 as an amber oil which crystallized on standing to form nearly colorless microcrystals: mp 100°-101° C. (lit14 mp not reported); IR: 1710 (carbonyl) cm-1 ; 1H NMR δ 0.982 (d, J=6.1 Hz, 3 H), 1.33 (d, J=7.1 Hz, 6 H), 2.0-2.7 (m, 5 H), 3.14 (sept, J=7.1 Hz, 1 H), 3.82 (s, 3 H), 3.85 (s, 3 H), 6.62 (d, J=8.0 Hz, 1 H), 6.75 (d, J=8.0 Hz, 1 H). Anal. (C16H24O4) C,H.
Workup
- filtrationfiltered through celite
- washthe celite was washed with ether
- customThe solvent was evaporated in a fume hood
- distillationthe residual oil was distilled bulb to bulb (170° C./1 torr)
Sources & evidence
- ORD record
- ord-a553f2527c1d40328efdaee53662982a
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05780675
Reaction notes
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