Potassium Glycolate → Oleylmethyldihydroxyethylammonium glycolate

HRID 1461642Notes

Reaction equation

HRID 1461642 reaction equation
[Cl-].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[C:26]([O-:30])(=[O:29])[CH2:27][OH:28].[K+]>C(O)C(C)C>[C:26]([O-:30])(=[O:29])[CH2:27][OH:28].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 23668515Potassium GlycolateHCID 86745345Oleylmethyldihydroxyethylammonium chloride

Product 1

HCID 86745353Oleylmethyldihydroxyethylammonium glycolateYield 93.4%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A four-necked flask fitted with stirrer and condenser means was charged with 40.5 g of oleylmethyldihydroxyethylammonium chloride, 12.0 g of potassium glycolate and 200 g of isobutyl alcohol and the reaction was conducted at 80°-85° C. in an atmosphere of nitrogen gas introduced at a low flow rate for 7 hours. The precipitate was then collected by filtration and washed with 30 ml of isobutyl alcohol. The filtrate and the washings were combined and concentrated under reduced pressure. The residue was dissolved in 200 g of toluene and filtered. The filtrate was then concentrated to give 41.0 g (theoretical yield 44.3 g) of oleylmethyldihydroxyethylammonium glycolate as a waxy product. The elemental analysis and infrared absorption data are given below.

Workup

  1. customA four-necked flask fitted with stirrer and condenser means
  2. customwas conducted at 80°-85° C. in an atmosphere of nitrogen gas
  3. additionintroduced at a low flow rate for 7 hours
  4. filtrationThe precipitate was then collected by filtration
  5. washwashed with 30 ml of isobutyl alcohol
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 200 g of toluene
  8. filtrationfiltered
  9. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-ea0817655c7a421e9adf03db6cba7a98
Source dataset
uspto-grants-1991_12
Patent number
US05076828

Reaction notes

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