N,N-Dimethylaniline → HCID 14068732, compound

HRID 352346Notes

Reaction equation

HRID 352346 reaction equation
C([O:4][C:5]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])C=C.CN(C)[C:17]1[CH:22]=CC=C[CH:18]=1>>[CH2:22]([C:12]1[C:5]([OH:4])=[C:6]([CH:9]=[CH:10][C:11]=1[O:13][CH3:14])[CH:7]=[O:8])[CH:17]=[CH2:18]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 107978122-allyloxy-4-methoxy-benzaldehyde

Product 1

HCID 14068732HCID 14068732, compound

Procedure

Heat a solution of 125 g of the product obtained in Step A in 300 ml of N,N-dimethylaniline at 200° C. for 15 hours. Then evaporate off the solvent in vacuo and take up the residue in 1 liter of isopropyl ether; extract the solution 10 times using 100 ml of 1N sodium hydroxide solution each time and then acidify the combined extracts using 3N hydrochloric acid. Then extract the aqueous acid solution with dichloromethane, and dry and concentrate the organic phase.

Workup

  1. customThen evaporate off the solvent in vacuo
  2. extractionextract the solution 10 times
  3. extractionThen extract the aqueous acid solution with dichloromethane
  4. customdry
  5. concentrationconcentrate the organic phase

Sources & evidence

ORD record
ord-63ae5f1428f142c4be6377684e229960
Source dataset
uspto-grants-2004_06
Patent number
US06747032B2

Reaction notes

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