Sodium Bicarbonate → HCID 22238274, compound

HRID 1743196Notes

Reaction equation

HRID 1743196 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[C:11]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1)(O)[CH:12]([CH3:14])[CH3:13].C(=O)([O-])O.[Na+]>Br>[CH:22]([C:19]1[CH:18]=[CH:17][C:16]([CH:11]2[C:4]3[CH:5]=[CH:6][C:7]([OH:9])=[CH:8][C:3]=3[O:2][C:12]2([CH3:14])[CH3:13])=[CH:21][CH:20]=1)([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 222382771-(2,4-Dimethoxyphenyl)-1-(4-isopropylphenyl)-2-methylpropan-1-ol

Product 1

HCID 22238274HCID 22238274, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 1-(2,4-dimethoxyphenyl)-1-(4-isopropylphenyl)-2-methylpropan-1-ol (5.58 g, 17.0 mmol) and 48% hydrobromic acid (30 mL) was heated under reflux for 24 hours in an argon atmosphere. After the reaction mixture was cooled, an aqueous saturated sodium hydrogencarbonate was added to the mixture, which was then extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=20/1 to 10/1) to obtain the title compound (2.43 g, yield 51%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours in an argon atmosphere
  3. temperatureAfter the reaction mixture was cooled
  4. extractionwas then extracted twice with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42786e5755e34482a04c4d939650be16
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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