Hydrochloric Acid → HCID 54690678, compound

HRID 982490Notes

Reaction equation

HRID 982490 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-a4dd2bd474614de8ae9206e7b5065490
Source dataset
uspto-grants-1991_02
Patent number
US04996301

Reaction notes

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