Iodoethane → 4-Ethoxy-3-hydroxybenzaldehyde

HRID 1427011Notes

Reaction equation

HRID 1427011 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH3:19]>CN(C)C=O>[CH2:18]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[OH:1])[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 756794-Ethoxy-3-hydroxybenzaldehydeYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Commercially available 3,4-dihydroxy benzaldehyde (35.8 g, 259 mmol) and potassium carbonate (37.6 g, 272 mmol) were dissolved in N,N-dimethylformamide (150 mL), then commercially available iodoethane (22 mL, 275 mmol) was added under nitrogen atmosphere at 0° C., and then the mixture was stirred for 2 days. The solvent was evaporated under vacuum, the resultant was cooled to 0° C., and then 5 M hydrochloric acid, ethyl acetate, and water were added for partition. The aqueous layer was extracted with ethyl acetate, the combined organic layer was washed with water twice and then with a saturated saline solution, and the mixture was dried over anhydrous magnesium sulfate and then filtered. The solvent was evaporated, then dichloromethane was added, and then the precipitate was collected by filteration to obtain the title compound (25.8 g, 60%). The filtrate was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-4:1-1:1). The target fraction was concentrated under vacuum, then diethyl ether and dichloromethane were added to the residue, and the precipitate was collected by filteration to obtain the title compound (3.45 g, 8.0%).

Workup

  1. customThe solvent was evaporated under vacuum
  2. addition5 M hydrochloric acid, ethyl acetate, and water were added
  3. customfor partition
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer was washed with water twice
  6. dry with materialwith a saturated saline solution, and the mixture was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated
  9. additiondichloromethane was added
  10. customthe precipitate was collected by filteration

Sources & evidence

ORD record
ord-853174a8a4ca47cc8f1cd93315491010
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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