Tetrahydrofuran → HCID 19080443, compound

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][C:14]([CH3:16])=[CH2:15])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].O1CCCC1>[C].[Pd].CO>[OH:12][C:11]1[CH:2]=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][C:10]=1[CH2:13][CH:14]([CH3:16])[CH3:15]

Participants

Procedure

Methyl 3-bromo-4-hydroxy-5-(2-methylprop-2-en-1-yl)benzoate (5.0 g, 24.2 mmol) and 10% palladium-carbon (50% water-containing product, 1.5 g) were added to a mixed solvent of tetrahydrofuran (70 mL) and methanol (70 mL), and the mixture was stirred under a hydrogen atmosphere at room temperature for 5 hr. The catalyst was filtered off, and the filtrate was concentrated to give the title compound (4.8 g, yield 95%) as colorless needle crystals.