Undecanoic Acid → Undecanoyl chloride

HRID 1779399Notes

Reaction equation

HRID 1779399 reaction equation
[C:1]([OH:13])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(Cl)(=O)C([Cl:17])=O>C(Cl)Cl.CN(C)C=O>[C:1]([Cl:17])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 8180Undecanoic AcidHCID 65578Oxalyl chloride

Product 1

HCID 87287Undecanoyl chlorideYield 39.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, a solution of 5.0 grams (0.027 mole) of undecanoic acid in 75 mL of methylene chloride was stirred and 2.8 ml (0.032 mole) of oxalyl chloride and 5 drops of N,N-dimethylformamide were added. Upon completion of addition, the reaction mixture was stirred for about 16 hours, then it was concentrated under reduced pressure, yielding 2.2 grams of undecanoyl chloride.

Workup

  1. additionUpon completion of addition
  2. concentrationit was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d422c28b3519402b8289ef0c496766fa
Source dataset
uspto-grants-1997_05
Patent number
US05627189

Reaction notes

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