6-(benzyloxy)-2,2-dimethylbenzofuran-3(2H)-one → 2,2-Dimethyl-2,3-dihydrobenzofuran-6-ol

HRID 545726Notes

Reaction equation

HRID 545726 reaction equation
C([O:8][C:9]1[CH:20]=[CH:19][C:12]2[C:13](=O)[C:14]([CH3:17])([CH3:16])[O:15][C:11]=2[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[CH3:16][C:14]1([CH3:17])[CH2:13][C:12]2[CH:19]=[CH:20][C:9]([OH:8])=[CH:10][C:11]=2[O:15]1

Participants

5

Reactant 2

HCID 666425186-(benzyloxy)-2,2-dimethylbenzofuran-3(2H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 200372932,2-Dimethyl-2,3-dihydrobenzofuran-6-olYield 88%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-(benzyloxy)-2,2-dimethylbenzofuran-3(2H)-one (0.85 g, 3.20 mmol) in methanol (100 mL) was added palladium hydroxide (0.22 g, 20 wt. % loading, 0.32 mmol). The resulting mixture was hydrogenated for 16 hours under 60 psi of hydrogen. The reaction mixture was filtered through celite, washed with methanol. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (ethyl acetate/hexane, 1/5) to give the title compound (0.46 g, 88%): 1H NMR (300 MHz, CDCl3) δ 6.92 (d, 1H), 6.30-6.21 (m, 2H), 4.77 (s, 1H), 2.90 (s, 2H), 1.44 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-b3c8330e741d41e193e26c5077cabb4b
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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