Reaction #2348135

ord-856cd64f0a5f413198dbd4061f6bead4

Reaction equation

CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)O
phytanic acid
O=S(Cl)Cl
thionyl chloride
→
CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)Cl
phytanic acid chloride
Yield 98.2%

Reactants

CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)O
phytanic acid
O=S(Cl)Cl
thionyl chloride

Reagents

c1ccncc1
pyridine

Solvents

ClCCl
methylene chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added dropwise
  2. 2
    Otherat room temperature
  3. 3
    workup.ADDITIONAfter the completion of dropwise addition
  4. 4
    Temperaturethe resultant was refluxed for 1 hour
  5. 5
    Concentrationconcentrated under reduced pressure

Procedure

Under a nitrogen atmosphere, one drop of pyridine was added to 2.5 g of phytanic acid and 12.5 ml of methylene chloride, and 1.43 g of thionyl chloride was added dropwise thereto at room temperature. After the completion of dropwise addition, the resultant was refluxed for 1 hour, and concentrated under reduced pressure to obtain about 2.6 g of phytanic acid chloride.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07846903B2uspto-grants-2010_12