Thionyl Chloride → HCID 131724893, compound

HRID 2182826Notes

Reaction equation

HRID 2182826 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=O)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O>[CH2:5]([O:12][C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([Cl:3])=[O:31])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 5427134516-(Benzyloxy)-16-oxohexadecanoic acid

Product 1

HCID 131724893HCID 131724893, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

One drop of dimethyl formamide and 2.32 ml of thionyl chloride were added to 3.01 g (8 millimoles) of the 1,14-tetradecane dicarboxylic acid monobenzyl ester obtained in Production Example 4. The reaction mixture was heated and allowed to reflux for one hour. Unreacted thionyl chloride was subsequently removed using distillation under reduced pressure to obtain 3.2 g of 1,14-tetradecane dicarboxylic acid monochloride monobenzyl ester in the form of a pale yellow liquid.

Workup

  1. customobtained in Production Example 4
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for one hour
  4. customwas subsequently removed
  5. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-9a067fb619ff4bb5b556bd09f0198485
Source dataset
uspto-grants-2005_05
Patent number
US06897326B2

Reaction notes

Loading…