3-Chloro-1,2-propanediol → HCID 53911827, compound

HRID 904490Notes

Reaction equation

HRID 904490 reaction equation
[CH2:1]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=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[CH2:39][CH:40]([OH:43])[CH2:41][OH:42]>O.CCOCC>[CH2:1]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:39][CH:40]([OH:43])[CH2:41][OH:42])=[O:21])=[CH:23][CH:24]=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 54267530HCID 54267530, compound

Product 1

HCID 53911827HCID 53911827, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7.35 g. of 4-(4-pentadecenyl)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 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-d2c2ef5b97894da0b0ed61d5a9d6bd75
Source dataset
uspto-grants-1980_10
Patent number
US04230878

Reaction notes

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