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

HRID 545732Notes

Reaction equation

HRID 545732 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-c5b4c2095b904da9a139e63e7e0b3f18
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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