Dimethylformamide → HCID 3572385, compound

HRID 1294096Notes

Reaction equation

HRID 1294096 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](I)[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:11]([O:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 709492,5-Dihydroxybenzaldehyde

Product 1

HCID 3572385HCID 3572385, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,5-dihydroxybenzaldehyde (9.81 g), ethyl iodide (13.29 g), anhydrous potassium carbonate (14.72 g) and N,N-dimethylformamide (100 mL) was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column a chromatography to give crystals (4.20 g, 36%) of 2-ethoxy-5-hydroxybenzaldehyde from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 108-109° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-46134f85759a48bca16487e70f6110e1
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…