Ethanolamine → 2-(4-Phenoxymethylphenoxy)-propionic acid

HRID 917901Notes

Reaction equation

HRID 917901 reaction equation
[O:1]([CH2:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:25]([CH2:27][NH2:28])[OH:26]>CN(P(N(C)C)(N(C)C)=O)C>[OH:26][CH2:25][CH2:27][NH-:28].[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 24386Thionyl ChlorideHCID 214211732-(4-Phenoxymethylphenoxy)-propionic acid

Product 2

HCID 214211732-(4-Phenoxymethylphenoxy)-propionic acidHCID 867336622-Hydroxyethylamide

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

2.72 g. of 2-(4-phenoxymethylphenoxy)-propionic acid is dissolved in 12 ml. of HMPA. At -10°, 0.77 ml. of thionyl chloride is added thereto, and the mixture is agitated for 2 hours at -5°. Thereafter, 2.5 ml. of ethanolamine is added and the reaction mixture is stirred overnight at 20°. The mixture is then poured on ice and worked up as usual, yielding the 2-hydroxyethylamide of 2-(4-phenoxymethylphenoxy)-propionic acid.

Workup

  1. customAt -10°
  2. stirringthe reaction mixture is stirred overnight at 20°
  3. additionThe mixture is then poured on ice

Sources & evidence

ORD record
ord-06cba50a81ab4a12858d628714511fe3
Source dataset
uspto-grants-1976_07
Patent number
US03968143

Reaction notes

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