Water → HCID 70625203, compound

HRID 1576138Notes

Reaction equation

HRID 1576138 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:15][C:16]([OH:22])(CO)[CH:17]([CH3:19])O.C1(C)C(C)=CC=CC=1.[OH2:31]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([C:8]2[O:10][CH:17]([CH3:19])[C:16]([OH:22])([OH:31])[N:15]=2)([CH3:12])[CH3:11])=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 962Water2×HCID 2797Clofibric AcidHCID 7237O-XyleneHCID 17802843HCID 17802843, compound

Product 1

HCID 70625203HCID 70625203, compoundYield 40%

Procedure

21.45 g. (0.1 moles) of 2-(p-chloro-phenoxy)-2-methyl-propionic acid and 15.14 g. (0.125 moles) of 2-amino-2-hydroxy-methyl-1,3-propane-diol are boiled for 12 hours in 900 ml. of anhydrous xylol in an apparatus provided with a water-separating column. The water formed during the course of the reaction is accumulated as an azeotropic mixture in the water-separating column from where it is removed from time to time. When no more water is evolved from the system the boiling is stopped. The hot xylene solution is discharged from the insoluble part. After cooling the white crystals precipitated from the xylene solution are filtered off and washed with benzene. After drying, the croude product obtained (21.8 g., Mp. 133°-135°C) is recrystallized from 70% aqueous ethanol. The pure product (12 g., yield 40%) has a mp. of 141.5°-142.5°C.

Workup

  1. customseparating column
  2. customThe water formed during the course of the reaction
  3. customseparating column from where it
  4. customis removed from time to time
  5. temperatureAfter cooling the white crystals
  6. customprecipitated from the xylene solution
  7. filtrationare filtered off
  8. washwashed with benzene
  9. customAfter drying
  10. customthe croude product obtained (21.8 g., Mp. 133°-135°C)
  11. customis recrystallized from 70% aqueous ethanol

Sources & evidence

ORD record
ord-54b8487e5d2f4e3aa9930c6bba1dbb30
Source dataset
uspto-grants-1976_09
Patent number
US03979405

Reaction notes

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