Sulfuric Acid → 5-Amino-2-benzyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran

HRID 234249Notes

Reaction equation

HRID 234249 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([OH:14])=[C:9]([CH3:15])[C:8]=1[CH3:16].[CH3:17][C:18](=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)CO.[C:28](=O)(O)[O-].[Na+]>ClCCl>[NH2:6][C:7]1[C:12]([CH3:13])=[C:11]([CH3:28])[C:10]2[O:14][C:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([CH3:17])[CH2:15][C:9]=2[C:8]=1[CH3:16]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5608792-Methyl-3-phenyl-2-propen-1-olHCID 111055374-Amino-2,3,5-trimethylphenol

Product 1

HCID 158169895-Amino-2-benzyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuranYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfuric acid (15 ml) was added to a solution of 4-amino-2,3,5-trimethylphenol (20.0 g, 0.13 mol) and 2-methyl-3-phenyl-2-propenol (25.0 g, 0.17 mol) in dichloromethane (100 ml) and the mixture was heated under reflux for 1 hour. The resulting reaction mixture was neutralized with aqueous saturated sodium bicarbonate solution and the product was extracted with ethyl acetate. The extract was washed with water and dried and then the solvent was distilled off. The residue was purified by silica gel column chromatography (isopropyl ether) and crystallized from hexane to obtain the desired compound (7.2 g, yield: 19.3%), m.p. 68°-69° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe resulting reaction mixture
  4. extractionthe product was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (isopropyl ether)
  9. customcrystallized from hexane

Sources & evidence

ORD record
ord-a03be0f97e264ef7af465c2008f818cc
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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