Hydrochloric Acid → 2-Decyltetradecanoyl chloride

HRID 1970098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970098
[CH2:1]([CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:12](O)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(Cl)(=O)C([Cl:30])=O.Cl>C1COCC1.CN(C)C=O>[CH2:1]([CH:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:12]([Cl:30])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 175556Decyltetradecanoic acid

Produkt 1

HCID 539445462-Decyltetradecanoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 100 mL round bottom flask is charged with 1.15 g (3.13 mmol) of 2-decyltetradecanoic acid (available as ISOCARB 24 from Sasol America), which is dissolved in 20 mL of THF with stirring under inert atmosphere. The solution is cooled to 0° C. and 1.1 mL (12.6 mmol) oxalyl chloride is added dropwise. Upon addition of N,N-dimethylformamide (DMF, 2-3 drops as catalyst), gaseous HCl is observed to evolve from the reaction mixture, after which the mixture is allowed to slowly warm to room temperature. Gas evolution ceases after 30 min, and the reaction is allowed to stir for an additional 30 min before removing solvent by rotary evaporation. The crude acid chloride is redissolved in 10 mL of fresh dry THF and then added dropwise and slowly to the appropriate amine solution, as described below.

Aufarbeitung

  1. temperatureto slowly warm to room temperature
  2. stirringto stir for an additional 30 min
  3. custombefore removing solvent
  4. customby rotary evaporation
  5. dissolutionThe crude acid chloride is redissolved in 10 mL of fresh dry THF
  6. additionadded dropwise and slowly to the appropriate amine solution

Quellen und Nachweise

ORD-Eintrag
ord-5cc1eae7e61b43a994729686d3212afb
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426636B2

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