Water → HCID 70625203, compound

HRID 1111858Notes

Reaction equation

HRID 1111858 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, compound

Procedure

21.45 g (0.1 moles) of 2-(p-chlorophenoxy)-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. anhydrous xylol in an appratus 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 crude product 2-[(p-chlorophenoxy)-isopropyl]-4,4-bis-hydroxy-methyl-2-oxazoline obtained (21.8 g, m.p.: 133°-135° C.) is recrystallized from 70% aqueous ethanol. The pure product (12 g, yield 40%) has a m.p. 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

Sources & evidence

ORD record
ord-31b2e1d0d05e47b1ab7ac22526610fb7
Source dataset
uspto-grants-1978_10
Patent number
US04119633

Reaction notes

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