3-Methoxybenzaldehyde → HCID 20523216, compound

HRID 223146Notes

Reaction equation

HRID 223146 reaction equation
[CH3:1]OC1C=C(C=CC=1)C=O.COC(OC)CN.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=1)[CH:23]=[N:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28].C[Mg]I>CCOCC.O.C1(C)C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=1)[CH:23]([NH:24][CH2:25][CH:26]([O:27][CH3:28])[O:29][CH3:30])[CH3:1]

Participants

8

Reactant 4

HCID 115693-MethoxybenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 1315411839964-84-6HCID 178418373HCID 178418373, compound

Product 1

HCID 20523216HCID 20523216, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 13.6 g. (0.1 mole) of 3-methoxybenzaldehyde and 10.5 g. (0.1 mole) of aminoacetaldehyde dimethyl acetal in 250 ml. of toluene is refluxed for one hour and water produced in the reaction is collected in a Dean-Stark trap. The resulting solution of 3-methoxy-N-(2,2-dimethoxyethyl)benzylidenamine is added to a solution of (0.2 mole) of methylmagnesium iodide in 250 ml. of ether over 1.5 hours. The mixture is stirred for one hour, cooled and quenched by careful addition of 250 ml. of water. The aqueous phase was filtered through Celite, extracted with 150 ml. of ether and the combined organic phases washed, dried and evaporated to yield 3-methoxy-α-methyl-N-(2,2-dimethoxyethyl)benzylamine.

Workup

  1. customis collected in a Dean-Stark trap
  2. temperaturecooled
  3. customquenched by careful addition of 250 ml
  4. filtrationThe aqueous phase was filtered through Celite
  5. extractionextracted with 150 ml
  6. washof ether and the combined organic phases washed
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-2627117ec5db4d90a634e2e9ed141d3a
Source dataset
uspto-grants-1982_10
Patent number
US04352809

Reaction notes

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