Dimethylformamide → HCID 14255179, compound

HRID 1744491Notes

Reaction equation

HRID 1744491 reaction equation
CN(C)C=O.Cl[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.[CH2:16]([OH:21])[C:17]([CH3:20])([CH3:19])[CH3:18].[H-].[Na+]>O>[CH2:16]([O:21][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6404Neopentyl alcoholHCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 14255179HCID 14255179, compoundYield 330.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dimethylformamide solution (78 ml) containing 4-chloronitrobenzene (15.7 g) and neopentyl alcohol (10.6 g) was added by portions sodium hydride (60% content, 4.8 g) under ice-cooling. The mixture was stirred under ice-cooling for 1 h. The mixture was warmed to room temperature and stirred further for 1 h. The reaction mixture was poured into water and extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The obtained oily substance was distilled under reduced pressure to give 4-neopentyloxynitrobenzene (69 g), boiling point: 120–125° C./0.1 mmHg.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 h
  3. stirringstirred further for 1 h
  4. extractionextracted with toluene
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent was evaporated under reduced pressure
  8. distillationThe obtained oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-b25ea2e4a4d24dc1ae9ffe74b62db9bd
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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