Acetic Acid → 3-(4-Isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1-benzofuran

HRID 1787114Notes

Reaction equation

HRID 1787114 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2OC)(O)[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Br.C(O)(=O)C.[OH2:28]>>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[O:28][C:11]2([CH3:13])[CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 231138311-(4-Isopropylphenyl)-1-(2-methoxyphenyl)-2-methylpropan-1-ol

Product 1

HCID 231138333-(4-Isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1-benzofuranYield 89%

Procedure

A mixture of 1-(4-isopropylphenyl)-1-(2-methoxyphenyl)-2-methylpropan-1-ol obtained in Reference Example 82 (3.4 g, 11.4 mmol), 48% hydrobromic acid (50 mL) and acetic acid (10 mL) was heated under reflux under argon atmosphere for 16 hours. After cooling, water was added to the reaction solution, which was extracted with ethyl acetate, and the combined organic layer was washed with water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 2.71 g (yield 89%) of the title compound. Oily matter.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under argon atmosphere for 16 hours
  3. temperatureAfter cooling
  4. extractionwas extracted with ethyl acetate
  5. washthe combined organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-7bd353d044cb4991b15f00dce48178be
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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