3-Methyl-1-benzofuran-5-ol → 3-Methyl-2,3-dihydrobenzofuran-5-ol

HRID 1504259Notes

Reaction equation

HRID 1504259 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1>O1CCCC1.[Pd]>[CH3:1][CH:2]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 1

HCID 135425263-Methyl-1-benzofuran-5-ol

Product 1

HCID 678954423-Methyl-2,3-dihydrobenzofuran-5-olYield 81.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Methyl-benzofuran-5-ol (prepared as above in EXAMPLE III) (245 g, 1.6 mol) was added in tetrahydrofuran (THF) (450 mL) and hydrogenated with palladium on carbon (Pd/C) (5%, 2.4 g) under hydrogen (H2) (200 psi) at 145° C. for about 8 hours till gas chromatograph (GC) analysis showed completion of the reaction. The obtained mixture was filtered and distilled to afford 3-methyl-2,3-dihydro-benzofuran-5-ol (190 g, 1.3 mol).

Workup

  1. customcompletion of the reaction
  2. filtrationThe obtained mixture was filtered
  3. distillationdistilled

Sources & evidence

ORD record
ord-c11bcba2ca1645d99619412d12e05742
Source dataset
uspto-grants-2015_12
Patent number
US09212336B2

Reaction notes

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