Eicosanoic Acid → Eicosanoyl chloride

HRID 514286Notes

Reaction equation

HRID 514286 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7](O)(=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]CC>CN(C=O)C.ClCCl>[C:2]([Cl:4])(=[O:3])[CH2:1][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

Participants

5

Reactant 2

HCID 10467Eicosanoic AcidHCID 65578Oxalyl chloride

Product 1

HCID 9862365Eicosanoyl chlorideYield 100.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Oxalyl chloride (2.67 ml, 0.0191 mol) was added drop-wise to a mixture of Arachidic acid (6.0 g, 0.0211 mol) and DMF (4 drops) in dichloromethane (50 ml) at 0° C. After the addition was completed, the reaction mixture was stirred at 0° C. for 30 minutes and then stirred at 25° C. for 1 hour, the reaction mixture was partitioned between dichloromethane and water, and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with brine, then dried with sodium sulphate and concentrated in vacuo to provide the desired product (6.35 g, 100% yield) as a solid which was not purified any further.

Workup

  1. additionAfter the addition
  2. stirringstirred at 25° C. for 1 hour
  3. customthe reaction mixture was partitioned between dichloromethane and water
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5f6671ad908457abd09f8683567ffdf
Source dataset
uspto-grants-2015_08
Patent number
US09107911B2

Reaction notes

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