3-Chloro-1,2-propanediol → HCID 20378383, compound

HRID 2051926Notes

Reaction equation

HRID 2051926 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)P(N(C)C)(N(C)C)=O.[OH-].[Na+].Cl[CH2:35][CH:36]([OH:39])[CH2:37][OH:38]>O.CCOCC>[O:1]([CH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH2:35][CH:36]([OH:39])[CH2:37][OH:38])=[O:17])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 72903-Chloro-1,2-propanediolHCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 20378378HCID 20378378, compound

Product 1

HCID 20378383HCID 20378383, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 5.5 g. of 4-(3-phenoxypropylamino)benzoic acid in 50 ml. of hexamethylphosphoramide is treated with 4.80 g. of 25% aqueous sodium hydroxide followed by 11.0 g. of 3-chloro-1,2-propanediol and then is heated at 140° C. for 6 hours. The mixture is diluted with water and ether and filtered to yield a white solid. Recrystallization from acetonitrile affords pure 2,3-dihydroxypropyl 4-(3-phenoxypropylamino)benzoate as a white crystalline solid.

Workup

  1. filtrationfiltered
  2. customto yield a white solid
  3. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-08ec3ebd93154dab8bce63e924f42d66
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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