Hydrochloric Acid → HCID 83815810, compound

HRID 854975Notes

Reaction equation

HRID 854975 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([CH3:10])[CH:4]=1)[CH3:2].[Mg+2].[Cl-].[Cl-].Cl.C[CH2:16][O:17]C(C)=O>CC#N.O>[CH2:1]([C:3]1[CH:4]=[C:5]([CH3:10])[C:6]([OH:9])=[C:7]([CH:8]=1)[CH:16]=[O:17])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 348574-Ethyl-o-cresolHCID 5360315Magnesium Chloride

Product 1

HCID 83815810HCID 83815810, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of the phenol of Example 150 Step 1 (5.0 g, 36.7 mmol) in 200 mL CH3CN, was added MgCl2 (5.25 g, 55.1 mmol), TEA (13.9 g, 19.2 mL, 137.6 mmol), and (CHO)N (8.3 g, 280 mmol). The reaction was heated at reflux for 3 h. After cooling, the reaction was diluted with EtOAc (500 mL) and acidified with aqueous 2N HCl until the reaction was pH 4. The reaction was diluted with 300 mL H2O. The organic layer was washed with H2O, with brine, dried over MgSO4, and concentrated. The residue was purified by flash chromatography (on SiO2, hexane/EtOAc=94/6) to give 3.2 g (53%) of the desired product as a clear oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 h
  3. temperatureAfter cooling
  4. washThe organic layer was washed with H2O, with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (on SiO2, hexane/EtOAc=94/6)

Sources & evidence

ORD record
ord-dacb886ea3ce4af390c2f9e7b405d630
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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