Tridecanoic acid → Tridecanoyl chloride

HRID 2082340Notes

Reaction equation

HRID 2082340 reaction equation
[C:1]([OH:15])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(Cl)(=O)C([Cl:19])=O>C1C=CC=CC=1>[C:1]([Cl:19])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 12530Tridecanoic acidHCID 65578Oxalyl chloride

Product 1

HCID 87288Tridecanoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 13.2 grams (61.5 mmol) of tridecanoic acid in 80 mL of benzene was added 26.2 grams (206 mmol) of oxalyl chloride. After stirring for 20 minutes, the mixture was heated to reflux and maintained at reflux overnight. The mixture was cooled to room temperature and the solvent was removed at reduced pressure to provide 14.3 grams (100%) of tridecanoyl chloride as an orange oil which was used without any further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux overnight
  5. customthe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-18e068ed3be24e6284db545d95ade90b
Source dataset
uspto-grants-1993_02
Patent number
US05189046

Reaction notes

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