Sodium;3-phenylprop-2-enoate → HCID 86745355, compound

HRID 1461644Notes

Reaction equation

HRID 1461644 reaction equation
[Cl-].[CH2:2]([NH2+:20][CH2:21][C:22]([OH:25])([OH:24])[OH:23])[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-:36])(=[O:35])[CH:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Na+]>C(O)C(C)C>[C:26]([O-:36])(=[O:35])[CH:27]=[CH:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1.[CH2:2]([NH2+:20][CH2:21][C:22]([OH:25])([OH:23])[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 517350Sodium;3-phenylprop-2-enoateHCID 86745349HCID 86745349, compound

Product 1

HCID 86745355HCID 86745355, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A four-necked flask fitted with stirrer and condenser means was charged with 43.3 g of oleyltrihydroxyethylammonium chloride, 20 g of sodium cinnamate and 200 g of isobutyl alcohol and the reaction was conducted at 40°-50° C. in an atmosphere of nitrogen gas introduced at a low flow rate for 6 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 and the residue was dissolved in 200 g of toluene and filtered. Finally, the filtrate was concentrated to give 50.9 g (theoretical yield 54.5 g) of oleyltrihydroxyethylammonium cinnamate as a waxy product. The elemental analysis is shown below.

Workup

  1. customA four-necked flask fitted with stirrer and condenser means
  2. customwas conducted at 40°-50° C. in an atmosphere of nitrogen gas
  3. additionintroduced at a low flow rate for 6 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. concentrationFinally, the filtrate was concentrated

Sources & evidence

ORD record
ord-514abe61e0c84765815283a57d163d10
Source dataset
uspto-grants-1991_12
Patent number
US05076828

Reaction notes

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