Sodium Iodide → HCID 68785352, compound

HRID 1957820Notes

Reaction equation

HRID 1957820 reaction equation
[CH3:1][CH:2](/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:22])=[C:18]([O:20][CH3:21])[CH:19]=1)=[O:11])[CH3:3].C([O-])([O-])=O.[K+].[K+].[I-].[Na+].P(O)([O-])([O-])=O.[Na+].[Na+].Br[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45]>CC(C)=O>[CH3:47][O:46][C:44](=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][O:22][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][NH:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH:4][CH:2]([CH3:1])[CH3:3])=[CH:19][C:18]=1[O:20][CH3:21]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 1548943CapsaicinHCID 4170292Methyl 6-Bromohexanoate

Product 1

HCID 68785352HCID 68785352, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of Capsaicin (2 g, 6.56 mmol), anhydrous K2CO3 (3 g, 22 mmol), sodium iodide (2 g, 13.3 mmol) and disodium phosphate (2 g, 14.2 mmol) in anhydrous acetone (50 ml) was added methyl 6-bromohexanoate (2 g, 9.6 mmol) and refluxed for 24 hours. Acetone was distilled off and water (15 ml) was added. Crude 12 was filtered, dried and purified by column chromatography on silica gel using benzene:ethyl acetate (9:1) to give pure 12 (1.5 g, 52.8%) as a pale white powder. The melting point was found to be 69.2-70.8° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. distillationAcetone was distilled off
  3. additionwater (15 ml) was added
  4. filtrationCrude 12 was filtered
  5. customdried
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-465c3e1469524c4fa9ea7e810f65fcea
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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