Ethanol → 84636-23-7

HRID 2366657Notes

Reaction equation

HRID 2366657 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].[CH2:20](O)[CH3:21]>>[ClH:3].[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 6966112-Aminododecanoic Acid

Product 1

HCID 5744705084636-23-7

Conditions

Temperature
0 °C

Procedure

Ethanol (150 mL) was cooled to 0° C., and thionyl chloride (16.57 mL, 139.3 mmol) was added over a period of ten minutes. The reaction was stirred for ten minutes at 0° C., and 12-aminododecanoic acid (25.0 g, 116 mol) was then added. The reaction was allowed to warm to ambient temperature, stirred at a slightly elevated temperature for one hour, and stirred at ambient temperature for two hours. The Ethanol was removed under reduced pressure, and the solid residue was recrystallized from ethyl acetate. The crystals were isolated by filtration, washed with diethyl ether, and dried under vacuum to provide 37.4 g of ethyl 12-aminododecanoate hydrochloride as a white solid.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred at a slightly elevated temperature for one hour
  3. stirringstirred at ambient temperature for two hours
  4. customThe Ethanol was removed under reduced pressure
  5. customthe solid residue was recrystallized from ethyl acetate
  6. customThe crystals were isolated by filtration
  7. washwashed with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-00f4c5b680e843569b24493d5e280534
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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