Hydrochloric Acid → HCID 58551018, compound

HRID 1908139Notes

Reaction equation

HRID 1908139 reaction equation
C([O-])([O-])=O.[K+].[K+].I[CH:8]([CH3:10])[CH3:9].[I:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([OH:19])=[C:14]([CH3:20])[CH:13]=1.Cl>CN(C=O)C>[I:11][C:12]1[CH:13]=[C:14]([CH3:20])[C:15]([O:19][CH:8]([CH3:10])[CH3:9])=[CH:16][C:17]=1[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 27362614-Iodo-2,5-dimethylphenol

Product 1

HCID 58551018HCID 58551018, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

K2CO3 (1.23 g, 8.87 mmol) followed by 2-iodopropane (806 μL, 8.06 mmol) were added to a solution of 4-iodo-2,5-dimethyl-phenol (1.00 g, 4.03 mmol) in DMF (40 mL) and the solution was heated at 50° C. for 24 h. The mixture was then acidified with 1% aq HCl before it was extracted with EtOAc (3×100 mL). The combined organics were washed with 1N NaOH (3×200 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (0-10% ethyl acetate/hexanes) to provide 1-iodo-4-isopropoxy-2,5-dimethylbenzene (42%) as a yellow oil.

Workup

  1. extractionwas extracted with EtOAc (3×100 mL)
  2. washThe combined organics were washed with 1N NaOH (3×200 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (0-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c6f110308709430f993b48466727b76d
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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