Water → 3-Ethoxybenzaldehyde

HRID 1784412Notes

Reaction equation

HRID 1784412 reaction equation
O[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:10](=[O:13])([O-])[O-].[K+].[K+].[CH2:16](I)C.O>CC(C)=O.C(OCC)(=O)C>[CH2:10]([O:13][C:9]1[CH:2]=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH:4]=[O:5])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 6998SalicylaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 899083-EthoxybenzaldehydeYield 90.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-hydroxybenzaldehyde (20 g, 163 mmol) in acetone (250 mL) was added anhydrous potassium carbonate (33 g, 239 mmol) followed by ethyl iodide (17 mL, 211 mmol). The mixture was heated at reflux for 12 hours. After cooling to room temperature water and ethyl acetate were added. The organic layer was removed, dried over MgSO4 and evaporated to dryness yielding the subtitled compound as a yellow oil (22.10 g). 1H NMR δ (CDCl3) 1.40-1.50 (3H, t), 4.024.15 (2H, q), 7.13-7.22 (1H, m), 7.36-7.48 (3H, m), 9.97 (1H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 hours
  3. additionwere added
  4. customThe organic layer was removed
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f05c9949114a4dd3856211b123cedfc6
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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