Acetone → LAB 181508

HRID 1939704Notes

Reaction equation

HRID 1939704 reaction equation
S([O-])([O-])(=O)=O.[OH:6][NH3+:7].O[NH3+].[CH3:10][C:11](C)=[O:12].[OH-:14].[Na+].Cl[CH2:17][C:18]([O:20][CH3:21])=[O:19].[C:22]1(C)[CH:27]=CC=C[CH:23]=1>O>[C:22](=[N:7][O:6][CH2:10][C:11]([O:12][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:14])([CH3:27])[CH3:23]

Participants

7

Reactant 5

HCID 180AcetoneHCID 1140TolueneHCID 7295Methyl chloroacetateHCID 14798Sodium Hydroxide2×HCID 24846Hydroxylamine sulfate

Product 1

HCID 188843LAB 181508

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

980 ml of water, 328 g of hydroxylammonium sulfate and 460 ml of toluene are initially introduced at from 20° to 50° C. and 232 g (4 mol) of acetone and 320 g (4 mol) of conc. sodium hydroxide solution are simultaneously added dropwise at pH 4.5 to 5.0. To complete the reaction, the mixture is stirred for about 1/2 hour and the phases are separated at from 30° to 40° C. The water phase is extracted twice by shaking with 460 ml of toluene. The entire organic phase is refluxed under reduced pressure (55° C.) at 100-200 mbar. For salt formation, 320 g (4 mol) of conc. sodium hydroxide solution are added dropwise and 250 g of water are simultaneously removed. Toluene is then distilled off at the same temperature and 2,000 ml of DMF are added. 466 g (4 mol) of Na chloroacetate are added to the crystal mash at 50° C. in portions and the mixture is stirred at 50° C. for 5 hours. 433 g (4 mol) of methyl chloroacetate are then added dropwise at from 50° to 55° C., stirring of the mixture is continued at 55° C. for 10 hours and DMF is then distilled over at the same temperature and under reduced pressure. The residue is taken up in toluene and washed with water. After a fractional distillation at 100° C./0.2 mm Hg, 531 g of final product are obtained. This corresponds to a total yield over all stages of 65.3% of theory. The product is obtained in a GC purity of 99.9% and has a refractive index nD20 of 1.4469.

Workup

  1. additionare simultaneously added dropwise at pH 4.5 to 5.0
  2. customthe reaction
  3. customthe phases are separated at from 30° to 40° C
  4. extractionThe water phase is extracted twice
  5. stirringby shaking with 460 ml of toluene
  6. custom250 g of water are simultaneously removed
  7. distillationToluene is then distilled off at the same temperature and 2,000 ml of DMF
  8. additionare added
  9. stirringthe mixture is stirred at 50° C. for 5 hours
  10. stirringstirring of the mixture
  11. waitis continued at 55° C. for 10 hours
  12. distillationDMF is then distilled over at the same temperature and under reduced pressure
  13. washwashed with water
  14. distillationAfter a fractional distillation at 100° C./0.2 mm Hg, 531 g of final product
  15. customare obtained
  16. customThis corresponds to a total yield over all stages of 65.3% of theory
  17. customThe product is obtained in a GC purity of 99.9%

Sources & evidence

ORD record
ord-52fdc497680342ac93f65288af9519b3
Source dataset
uspto-grants-1997_12
Patent number
US05696283

Reaction notes

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