Acetic Acid → 5-Cyano-2-methoxybenzaldehyde

HRID 745252Notes

Reaction equation

HRID 745252 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:6]#[N:7].C1N2CN3CN(C2)CN1C3.C(O)(=[O:25])C.Cl>O>[C:6]([C:5]1[CH:4]=[C:3]([C:10]([O:11][CH3:12])=[CH:9][CH:8]=1)[CH:2]=[O:25])#[N:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 136553283-(Bromomethyl)-4-methoxybenzonitrile

Product 1

HCID 102410985-Cyano-2-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 g of 3-bromomethyl-4-methoxybenzonitrile, were added 6.2 g of hexamethylenetetramine, 10 ml of acetic acid, and 10 ml of water. The mixture was heated under reflux for 2 hours. After addition of 10 ml of concentrated hydrochloric acid, the mixture was further refluxed for 15 minutes. The reaction mixture was cooled in ice and extracted with 200 ml of ethyl acetate. The ethyl acetate layer was washed twice with 200 ml of water, then with saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. Ether was added to the residue and the precipitated crystals were collected by filtration to yield 1.6 g of 3-cyano6-methoxybenzaldehyde; m.p. 119°-120° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture was further refluxed for 15 minutes
  4. temperatureThe reaction mixture was cooled in ice
  5. extractionextracted with 200 ml of ethyl acetate
  6. washThe ethyl acetate layer was washed twice with 200 ml of water
  7. dry with materialwith saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. additionEther was added to the residue
  11. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-3d08d73c5279455798db88a8d55acca6
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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