Benzyl Chloride → 3-(Benzyloxy)-4-ethoxybenzaldehyde

HRID 2360952Notes

Reaction equation

HRID 2360952 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[OH:12])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[O:12][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 756794-Ethoxy-3-hydroxybenzaldehyde

Product 1

HCID 8185733-(Benzyloxy)-4-ethoxybenzaldehydeYield 83.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

16.6 grams of 4-ethoxy-3-hydroxybenzaldehyde (100 mmol.) and 200 ml of absolute ethyl alcohol are added to a three-necked flask and then heated to 40° C. for being dissolved, 9 grams of potassium carbonate (65.07 mmol.) is added, 15 ml of benzyl chloride (130.13 mmol.) is added under stirring, heating reflux is performed for 1 hour, the reaction product is cooled to 50° C. after complete reaction is detected by TLC and then filtered while it is hot, the filtrate is put in a refrigerator for being cooled over night, crystals are separated out and pump-filtered, filter cakes are washed with 30 mL of absolute ethyl alcohol and then vacuum-dried to obtain 21.5 grams of white needle crystals, and the yield is 83.9%.

Workup

  1. dissolutionfor being dissolved
  2. temperatureheating
  3. temperaturereflux
  4. temperaturethe reaction product is cooled to 50° C.
  5. customafter complete reaction
  6. filtrationfiltered while it
  7. temperaturefor being cooled over night
  8. customcrystals are separated out
  9. filtrationpump-filtered
  10. filtrationfilter cakes
  11. washare washed with 30 mL of absolute ethyl alcohol
  12. customvacuum-dried

Sources & evidence

ORD record
ord-2f05b01c0e674fc6908fbae147c78e01
Source dataset
uspto-grants-2014_04
Patent number
US08686187B2

Reaction notes

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