Hydrochloric Acid → HCID 54690678, compound

HRID 1614502Notes

Reaction equation

HRID 1614502 reaction equation
[O:1]([CH2:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH2:16][C:15](=[O:20])[O:14]1.N1C=CC=CC=1.Cl>C(Cl)Cl.O>[OH:10][C:9](=[C:16]1[C:17](=[O:19])[O:18][C:13]([CH3:21])([CH3:12])[O:14][C:15]1=[O:20])[CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 69703Phenoxyacetyl chloride

Product 1

HCID 54690678HCID 54690678, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

93.8 g (0.55 mol) of phenoxyacetyl chloride are added dropwise to a solution, cooled to 8° C., of 72.1 g (0.5 mol) of 2,2-dimethyl-1,3-dioxane-4,6-dione and 79.1 g (1.0 mol) of pyridine in 250 ml of methylene chloride so that the temperature does not rise above 10° C. The mixture is subsequently stirred at room temperature for 2.5 hours, a mixture of 250 g of ice, 250 ml of water and 30 ml of concentrated hydrochloric acid is added and the mixture is extracted by shaking. The organic phase is washed twice with 100 ml of water each time and dried over magnesium sulfate. The solvent is distilled off, a solid remaining, which is recrystallized from t-butyl methyl ether. 72 g (52% of theory) of white crystals of the compound (6), which melt at 85°-87° C., with decomposition, are obtained.

Workup

  1. customdoes not rise above 10° C
  2. additionis added
  3. extractionthe mixture is extracted
  4. stirringby shaking
  5. washThe organic phase is washed twice with 100 ml of water each time
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customa solid remaining, which is recrystallized from t-butyl methyl ether
  9. customare obtained

Sources & evidence

ORD record
ord-c8cfc079aac84ede9c11c8287b7f3a62
Source dataset
uspto-grants-1993_03
Patent number
US05198322

Reaction notes

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