Formic Acid → 2,2,4,5,6-Pentamethyl-2,3-dihydrobenzofuran

HRID 234274Notes

Reaction equation

HRID 234274 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([CH3:9])[C:7]=1[CH3:8].[CH3:11][C:12](=[CH2:15])[CH2:13]O.C(O)=O>C(OC(C)C)(C)C>[CH3:11][C:12]1([CH3:15])[CH2:13][C:3]2[C:2]([CH3:1])=[C:7]([CH3:8])[C:6]([CH3:9])=[CH:5][C:4]=2[O:10]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 10557Methallyl alcoholHCID 106963,4,5-Trimethylphenol

Product 1

HCID 190785652,2,4,5,6-Pentamethyl-2,3-dihydrobenzofuranYield 41.5%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

3,4,5-Trimethylphenol (5.0 g, 36.7 mmol) and 2-methyl-2-propenol (3.2 g, 44.0 mmol) were added to formic acid (50 ml). The mixture was heated under reflux for 3 hours. The reaction mixture was diluted with isopropyl ether, washed with water and saturated sodium bicarbonate solution, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 97:3) to obtain the desired compound (2.9 g, yield: 41.5%) as oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. washwashed with water and saturated sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 97:3)

Sources & evidence

ORD record
ord-d4c50b54ef084ae8a727fc0a919300b1
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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