Vanillin → 4-Ethoxy-3-methoxybenzaldehyde

HRID 2360951Notes

Reaction equation

HRID 2360951 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[CH:12](O)(C)[CH3:13].[OH-].[Na+]>C1OCCOCCOCCOCCOCCOC1.O>[CH2:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11])[CH3:13]

Participants

6

Reactant 3

HCID 1183VanillinHCID 3776IsopropanolHCID 14798Sodium Hydroxide

Product 1

HCID 671164-Ethoxy-3-methoxybenzaldehydeYield 92%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

76 grams of 4-hydroxy-3-methoxybenzaldehyde (0.5 mol) and 500 mL of isopropanol are added into a four-necked flask and then stirred for 20 minutes, a constant pressure dropping funnel is used for slowly dropping 150 milliliters of aqueous solution of 6.5 grams of 18-crown-6 ether and 133 grams of sodium hydroxide, and stirring is performed for 30 minutes, the reaction system is heated to 60° C., at which 85 grams of bromethyl is dropped for reacting for 5 to 6 hours while TLC tracking is implemented, after the reaction ends, the reaction system is cooled (to 15° C.) and is added with 500 mL of water for stopped reaction, the product is extracted by ether (3×300 mL), organic phase is washed with water to be neutral, anhydrous MgSO4 is dried, ether is partially distilled, a large amount of petroleum ether is added to precipitate crude product, the crude product is subjected to recrystallization by ether/petroleum ether to obtain 83 grams of 4-ethoxy-3-methoxybenzaldehyde:, and the yield is 92%.

Workup

  1. stirringstirring
  2. waitis performed for 30 minutes
  3. additionis dropped
  4. waitfor reacting for 5 to 6 hours while TLC tracking
  5. temperaturethe reaction system is cooled (to 15° C.)
  6. customreaction
  7. extractionthe product is extracted by ether (3×300 mL), organic phase
  8. washis washed with water
  9. dry with materialanhydrous MgSO4 is dried
  10. distillationether is partially distilled
  11. additiona large amount of petroleum ether is added
  12. customto precipitate crude product
  13. customthe crude product is subjected to recrystallization by ether/petroleum ether

Sources & evidence

ORD record
ord-70529309a4ec4f2381a7a403e021e8e9
Source dataset
uspto-grants-2014_04
Patent number
US08686187B2

Reaction notes

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