Ethanol → HCID 12923606, compound

HRID 1395589Notes

Reaction equation

HRID 1395589 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[OH-].[Na+].[CH2:20](O)[CH3:21]>>[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([O:5][CH2:20][CH3:21])=[O:4]

Participants

5

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 30792384276-16-4

Product 1

HCID 12923606HCID 12923606, compoundYield 75%

Procedure

2-Aminodecanoic acid (J. Am. Chem. Soc., 1946, 68, 450) (16.0 g) was added in portions to a cooled (-10° C.) mixture of absolute ethanol (70 ml) and thionyl chloride (6 ml) with stirring. The resulting solution was set aside for 2 hours, at room temperature, refluxed for 1 hour, cooled, poured into ice-water, and the pH of the solution was adjusted to 9 with aqueous sodium hydroxide. The mixture was extracted with ether, the extract was dried, concentrated, then distilled, giving ethyl 2-aminodecanoate (75%) as a colourless oil, b.p. 82°-84° C./0.2 mm.

Workup

  1. temperaturea cooled
  2. temperaturerefluxed for 1 hour
  3. temperaturecooled
  4. extractionThe mixture was extracted with ether
  5. customthe extract was dried
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-b9665060f1944271ac22f5e4b0281d06
Source dataset
uspto-grants-1980_05
Patent number
US04204068

Reaction notes

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