Acetone → 2,5-Diethoxybenzaldehyde

HRID 565185Notes

Reaction equation

HRID 565185 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].N#N.I[CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+].[CH3:22][C:23](C)=O>>[CH2:22]([O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][CH3:15])=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:23]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 131722258HCID 131722258, compound

Product 1

HCID 34343142,5-Diethoxybenzaldehyde

Procedure

A suspension of 9.66 g (70 mmol) 2,5-dihydroxybenzaldehyde N2, 32.75 g (210 mmol) iodoethane, 24.19 g (175 mmol) K2CO3 in 350 ml acetone was heated to reflux for 18 hours under nitrogen. The solvent was evaporated and the residue was dissolved in 300 ml CHCl3 and 300 ml water. The organic phase was washed with 2×300 ml 2.5% Na2CO3 and 300 ml saturated NaCl and dried over Na2SO4. The solvent was evaporated and the residue (13.5 g) purified with a silica gel column (silica gel 100, CHCl3/cyclohexane: 1/1, v/v), affording 8.61 g light yellow oil, which crystallized after cooling to room temperature (yield. 63%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours under nitrogen
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in 300 ml CHCl3
  5. washThe organic phase was washed with 2×300 ml 2.5% Na2CO3 and 300 ml saturated NaCl
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated
  8. customthe residue (13.5 g) purified with a silica gel column (silica gel 100, CHCl3/cyclohexane
  9. custom1/1, v/v), affording 8.61 g light yellow oil, which
  10. customcrystallized
  11. custom(yield. 63%)

Sources & evidence

ORD record
ord-43be5279e9e04366bc268cabc1c361b6
Source dataset
uspto-grants-2001_01
Patent number
US06171866B2

Reaction notes

Loading…