Ethanol → Ethyl-11-iodoundecanoate

HRID 217087Notes

Reaction equation

HRID 217087 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH2:15](O)[CH3:16].OS(O)(=O)=O>C1(C)C=CC=CC=1>[CH2:15]([O:13][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][I:1])[CH3:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1146110411-iodoundecanoic Acid

Product 1

HCID 171303Ethyl-11-iodoundecanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

11-Iodo-undecanoic acid ethyl ester was synthesized according to Bergbreiter, J. Org. Chem., 40/6 (1975) 779. Briefly, 246.6 g 11-Iodo undecanoic acid, 440 ml dry ethanol, 440 ml dry toluol and 5 ml H2SO4 (98%) were combined. The mixture was distilled whereby about 400 ml aceotrope was removed at 75° C. or 76° C., respectively. Then 15 g K2CO3 was added and after 5 min the mixtures was filtered and finally distilled at a bath temperature of 115° C. The resulting brown oil was purified by filtration through a frit filled with silica gel (eluent: acetic acid ethyl ester/petrol ether 1:7). The final product was characterized by 1H-NMR and thin layer chromatography.

Workup

  1. distillationThe mixture was distilled whereby about 400 ml aceotrope
  2. customwas removed at 75° C. or 76° C.
  3. additionThen 15 g K2CO3 was added and after 5 min the mixtures
  4. filtrationwas filtered
  5. distillationfinally distilled at a bath temperature of 115° C
  6. filtrationThe resulting brown oil was purified by filtration through a frit
  7. additionfilled with silica gel (eluent: acetic acid ethyl ester/petrol ether 1:7)

Sources & evidence

ORD record
ord-b87703d2b4f54196a4cfb000158fdc98
Source dataset
uspto-grants-2012_06
Patent number
US08193246B2

Reaction notes

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