Water → HCID 86625159, compound

HRID 1663364Notes

Reaction equation

HRID 1663364 reaction equation
[N+:1]([C:4]1[C:5]([OH:15])=[C:6]([O:12][CH2:13][CH3:14])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:13]([O:12][C:6]1[CH:7]=[C:8]([CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[O:15][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([O:17][CH3:16])[CH:19]=1)[CH:9]=[O:10])[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 86625159HCID 86625159, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-nitro-3-ethoxy-4-hydroxybenzaldehyde (100 mg), 3-methoxybenzyl bromide (73 μl), potassium carbonate (144 mg) and tetrabutylammonium iodide (10 mg) in DMF (5 ml) was stirred at 60° C. for 90 min. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 2/1 (v/v) as eluent.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 2/1 (v/v) as eluent

Sources & evidence

ORD record
ord-d95001f1685b4a218fbf15ee1a4ebe87
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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