Hydrochloric Acid → 2-Decyltetradecanoyl chloride

HRID 1014895Notes

Reaction equation

HRID 1014895 reaction equation
[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]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 175556Decyltetradecanoic acid

Product 1

HCID 539445462-Decyltetradecanoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5cca6bb371ec4463a6f4576a89e7e32c
Source dataset
uspto-grants-2011_07
Patent number
US07985290B2

Reaction notes

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