P-Cresol → HCID 54566991, compound

HRID 2255556Notes

Reaction equation

HRID 2255556 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[H][H].Br[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:13]([O:15][CH3:16])=[O:14]>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:18]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=2[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:1][CH:2]=1

Participants

6

Reactant 3

HCID 2879P-CresolHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 54566991HCID 54566991, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Procedure

To a 0° C. suspension of KH (530 mg, 1.0 eq) in DMF (10 mL) was quickly added p-cresol (500 mg, 4.63 mmol), and the reaction mixture was stirred at room temperature. After stirring 10 minutes hydrogen evolution had subsided, and 50 mg of 18-crown-6 was added followed by the product of Step A (1.22 g, 1.0 eq). The reaction mixture was stirred 2.5 hours and was then concentrated in vacuo. The residue was purified on a silica gel flash chromatography column (140×30 mm) eluted with 5% ethyl acetate/hexane to yield 0.744 g (55%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred 2.5 hours
  2. concentrationwas then concentrated in vacuo
  3. customThe residue was purified on a silica gel flash chromatography column (140×30 mm)
  4. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b21fc81f3fe5413e83e6af320ea593d6
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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