Water → HCID 22933644, compound

HRID 1269833Notes

Reaction equation

HRID 1269833 reaction equation
C(N(CC)C(C)C)(C)C.ClCO[CH2:13][O:14][CH2:15][O:16][CH2:17]Cl.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23]C=1O.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:17]=1[O:16][CH2:15][O:14][CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 767382-Methoxy-4-nitrophenolHCID 81531DiisopropylethylamineHCID 22246685HCID 22246685, compound

Product 1

HCID 22933644HCID 22933644, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

N,N-diisopropylethylamine (1.24 ml, 7.09 mmol), chloromethoxymethyl ether (0.494 ml, 6.50 mmol) and tetrabutylammonium bromide (218 mg, 0.591 mmol) were added to a solution of 2-methoxy-4-nitrophenol (1.0 g, 5.91 mmol) in dichloromethane (20 ml) at 0° C. After 1 hour, the mixture thus obtained was warmed up to room temperature. After 15 hours, the mixture was poured into water (50 ml) and extracted with chloroform (50 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 2-methoxy-1-(methoxymethoxy)-4-nitrobenzene (1.26 g, 100%).

Workup

  1. customthe mixture thus obtained
  2. waitAfter 15 hours
  3. extractionextracted with chloroform (50 ml×2)
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe organic layer dried
  6. concentrationwas concentrated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-81e8f5d32ca045f082200ba49d0afa8a
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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