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

HRID 2376296Notes

Reaction equation

HRID 2376296 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-bcaf4302ec0f4197a7bcc43f5840c45f
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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