Potassium Iodide → 4'-(Methoxymethoxy)-2',6'-dimethylbiphenyl-3-carbaldehyde

HRID 273381Notes

Reaction equation

HRID 273381 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1.[CH3:18][O:19][CH2:20]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:18][O:19][CH2:20][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

Product 1

HCID 231573064'-(Methoxymethoxy)-2',6'-dimethylbiphenyl-3-carbaldehydeYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (4.5 g, 19.9 mmol), chloromethyl methyl ether (2.3 mL, 30.3 mmol), potassium carbonate (5.5 g, 39.8 mmol) and potassium iodide (0.66 g, 3.98 mmol) in N,N-dimethylformamide (50 mL) was stirred at 70° C. for 20 hrs. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:97-1:9) to give the title compound (1.7 g, yield 32%) as a colorless oil.

Workup

  1. washwashed successively with aqueous citric acid solution, water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:97-1:9)

Sources & evidence

ORD record
ord-2219d23b38734d67b4878eba4edc2006
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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