Sodium Iodide → 4-(2-Iodoethyl)-1,1-dimethylcyclohexane

HRID 397721Notes

Reaction equation

HRID 397721 reaction equation
BrC1C=CC(S(O[CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)(=O)=O)=CC=1.[I-:22].[Na+]>CC(C)=O>[I:22][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 23000956HCID 23000956, compound

Product 1

HCID 230009084-(2-Iodoethyl)-1,1-dimethylcyclohexaneYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(4,4-dimethylcyclohexyl)ethyl 4-bromobenzenesulfonate (Preparation 16, 410 mg, 1 mmol) in acetone (100 ml) was added sodium iodide (370 mg, 2.5 mmol), and the mixture was heated under reflux for 3 h. After allowing the reaction mixture to cool to room temperature, the mixture was filtered and the filtrate was diluted with water (500 ml) and extracted with diethyl ether (500 ml). The organic extract was dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a colourless oil (220 mg, 83%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. filtrationthe mixture was filtered
  4. additionthe filtrate was diluted with water (500 ml)
  5. extractionextracted with diethyl ether (500 ml)
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-325b46b2db94438d98754737fb9390a0
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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