Acetic Anhydride → 3-Methyl-4-acetoxybenzofuran

HRID 1607277Notes

Reaction equation

HRID 1607277 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:11])=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(N(CC)CC)C>O1CCCC1>[CH3:1][C:2]1[C:6]2[C:7]([O:11][C:12](=[O:14])[CH3:13])=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 110080683-Methyl-1-benzofuran-4-ol

Product 1

HCID 145797933-Methyl-4-acetoxybenzofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-methyl-4-hydroxybenzofuran (5.0 gm, 34.7 mmoles), acetic anhydride (50 mL) and triethylamine (25 mL) in tetrahydrofuran (150 mL) was stirred at room temperature overnight. The volatiles were removed in vacuo and the residue was purified by chromatography on silica gel. Elution with 15% ethylacetate in hexane yielded 3-methyl-4-acetoxybenzofuran.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by chromatography on silica gel
  3. washElution with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-69396100fb174d618f6d5b7d7400c5e1
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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