Water → HCID 20559517, compound

HRID 972066Notes

Reaction equation

HRID 972066 reaction equation
C1[O:10][C:4]([CH2:6][CH2:7][CH2:8]Cl)([CH3:5])OC1.[CH3:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+].O>C1(C)C=CC=CC=1>[CH3:11][N:12]([CH2:8][CH2:7][CH2:6][C:4](=[O:10])[CH3:5])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7515N-MethylanilineHCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolaneHCID 516892Sodium Bicarbonate

Product 1

HCID 20559517HCID 20559517, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 49.4 g (0.30 mol) 5-chloro-2-pentanone ethylene ketal and 64.2 g (0.60 mol) N-methylaniline in 100 ml toluene, add 27.7 g (0.33 mol) NaHCO3 and 2.0 g KI. Reflux with a water separator overnight. Allow to cool, filter, and concentrate. Distill at 50°/0.1 mm to remove N-methylaniline. Stir the residual liquid with 175 ml 1.0 N HCl for 2 hrs. Neutralize with NaHCO3 and extract with ether. Dry, concentrate, and distill to collect a fraction of b.p. 103°-110° /0.1 mm.

Workup

  1. temperatureto cool
  2. filtrationfilter
  3. concentrationconcentrate
  4. distillationDistill at 50°/0.1 mm
  5. customto remove N-methylaniline
  6. extractionNeutralize with NaHCO3 and extract with ether
  7. customDry
  8. concentrationconcentrate
  9. distillationdistill
  10. customto collect a fraction of b.p. 103°-110° /0.1 mm

Sources & evidence

ORD record
ord-dd25a3e2508944d8a12f36f1a9a85fc2
Source dataset
uspto-grants-1979_07
Patent number
US04163053

Reaction notes

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