Undecanoic Acid → Undecanoyl chloride

HRID 1081643Notes

Reaction equation

HRID 1081643 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-fdf23f79055d41ccb7508db74a302152
Source dataset
uspto-grants-1996_12
Patent number
US05587379

Reaction notes

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