6-(Benzyloxy)-3,3-dimethyl-2,3-dihydrobenzofuran → 3,3-Dimethyl-2,3-dihydro-1-benzofuran-6-ol

HRID 425514Notes

Reaction equation

HRID 425514 reaction equation
C([O:8][C:9]1[CH:19]=[CH:18][C:12]2[C:13]([CH3:17])([CH3:16])[CH2:14][O:15][C:11]=2[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:16][C:13]1([CH3:17])[C:12]2[CH:18]=[CH:19][C:9]([OH:8])=[CH:10][C:11]=2[O:15][CH2:14]1

Participants

5

Reactant 2

HCID 666426176-(Benzyloxy)-3,3-dimethyl-2,3-dihydrobenzofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 214852193,3-Dimethyl-2,3-dihydro-1-benzofuran-6-olYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-(benzyloxy)-3,3-dimethyl-2,3-dihydrobenzofuran (3.48 g, 13.7 mmol) in methanol (200 mL) was added Pd/C (1.45 g) and the mixture was hydrogenated under 40 psi of hydrogen overnight. 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, 1/7) to give the title compound (1.66 g, 74%): MS (ES+) m/z 165.4 (M+1).

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-2446f4df1b7a4a22abc0ea809cfba3c5
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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