Sodium Iodide → Methyl 12-iodododecanoate

HRID 2400306Notes

Reaction equation

HRID 2400306 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Br.[I-:17].[Na+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][I:17]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 11022721Dodecanoic acid, 12-bromo-, methyl ester

Product 1

HCID 13181482Methyl 12-iodododecanoateYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

12-Bromododecanoic acid methyl ester (5.65 g, 19.3 mmol) was dissolved in acetone (50 ml). Sodium iodide (14.4 g, 96 mmol) was added and the reaction was refluxed under nitrogen for 20 h. The sample was concentrated under vacuum. Water (100 ml) was added, and the mixture was extracted with AcOEt (2×100 ml). The organic extracts were pooled and washed with water plus a small amount of sat. NaCl and sat. NaCl (100 ml each), dried over MgSO4, and concentrated to yield a light yellow oil (6.37 g, 97%).

Workup

  1. temperaturethe reaction was refluxed under nitrogen for 20 h
  2. concentrationThe sample was concentrated under vacuum
  3. additionWater (100 ml) was added
  4. extractionthe mixture was extracted with AcOEt (2×100 ml)
  5. washwashed with water
  6. dry with materiala small amount of sat. NaCl and sat. NaCl (100 ml each), dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8304291f32ef4dfd9888a6b4e466d619
Source dataset
uspto-grants-2014_08
Patent number
US08796205B2

Reaction notes

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