Dichloromethane → 5-(3-Hydroxypropoxy)-2-nitrobenzaldehyde

HRID 1935305Notes

Reaction equation

HRID 1935305 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[OH:6][C:7]1[CH:8]=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[C:11]([CH:14]=1)[CH:12]=[O:13].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>C(#N)C>[N+:15]([C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:2][CH2:3][CH2:4][OH:5])=[CH:14][C:11]=1[CH:12]=[O:13])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 392115-Hydroxy-2-nitrobenzaldehyde

Product 1

HCID 226397485-(3-Hydroxypropoxy)-2-nitrobenzaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Bromo-1-propanol (3.34 g, 24 mmol) was refluxed in 80 ml of anhydrous acetonitrile with 5-hydroxy-2-nitrobenzaldehyde (3.34 g, 20 mmol), K2CO3 (3.5 g), and KI (100 mg) overnight (15 hr). The reaction mixture was cooled to room temperature and 150 ml of methylene chloride was added. The mixture was filtered and the solid residue was washed with methylene chloride. The combined organic solution was evaporated to dryness and redissolved in 100 ml methylene chloride. The resulted solution was washed with saturated NaCl solution and dried over sodium sulfate. 4.31 g (96%) of desired product was obtained after removal of the solvent in vacuo.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid residue was washed with methylene chloride
  3. customThe combined organic solution was evaporated to dryness
  4. dissolutionredissolved in 100 ml methylene chloride
  5. washThe resulted solution was washed with saturated NaCl solution
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-da1f2d21e7b94e9892387b5ad96bada7
Source dataset
uspto-grants-2002_05
Patent number
US06387628B1

Reaction notes

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