3-Chloro-1,2-propanediol → HCID 54408885, compound

HRID 1278296Notes

Reaction equation

HRID 1278296 reaction equation
[CH2:1]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].CN(C)P(N(C)C)(N(C)C)=O.[OH-].[Na+].Cl[CH2:41][CH:42]([OH:45])[CH2:43][OH:44]>O.CCOCC>[CH2:1]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH2:41][CH:42]([OH:45])[CH2:43][OH:44])=[O:25])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 72903-Chloro-1,2-propanediolHCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 54026116HCID 54026116, compound

Product 1

HCID 54408885HCID 54408885, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.35 g. of 4-(4-pentadecenyl)aminophenylacetic 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 and then from carbon tetrachloride affords the product as a white solid.

Workup

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

Sources & evidence

ORD record
ord-d88e6a9db3e241c9b767daa354f023e6
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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