Acetic Anhydride → 7-Methyl-2,3-dihydrobenzofuran

HRID 469365Notes

Reaction equation

HRID 469365 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][CH2:8][CH:7](O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C>C(O)(=O)C.[Pd]>[CH3:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 130130607-Methyl-2,3-dihydro-1-benzofuran-3-ol

Product 1

HCID 225923867-Methyl-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Under a nitrogen atmosphere 0.610 g (4.06 mmol) 7-methyl-2,3-dihydro-benzofuran-3-ol in 5 mL acetic acid were refluxed for 2 h with 770 μL (8.16 mmol) acetic anhydride. After cooling to RT, 60 mg palladium on charcoal (Pd/C 10%) were added and the mixture was hydrogenated for 3.5 h under a hydrogen atmosphere (3 bar). The catalyst was filtered off and the solvent was evaporated down.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated down

Sources & evidence

ORD record
ord-2580585de82f4784a33216fd905e875c
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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