Sodium Iodide → 2-(2-iodoethyl)-2-methyl-1,3-dioxolane

HRID 393456Notes

Reaction equation

HRID 393456 reaction equation
[CH2:1]1[O:9][C:4]([CH2:7][CH3:8])([CH2:5]Br)[O:3][CH2:2]1.[I-:10].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH2:1]1[O:9][C:4]([CH2:7][CH2:8][I:10])([CH3:5])[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 12938388HCID 12938388, compound

Product 1

HCID 110320462-(2-iodoethyl)-2-methyl-1,3-dioxolaneYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4 bromo-2-butanone ethylene ketal (16.4 mmol,3.2 g) in acetone (30 mL) was treated with sodium iodide (24 mmol, 3.7 g) and sodium carbonate (50 mmol, 5.1 g) and was reluxed overnight. The resulting mixture was filtered, washed with acetone (10 mL) and evaporated to dryness to a white solid. The residue was triturated with a mixture of 1:1 ether: pet ether (20 mL), stirred 30 min., filtered and evaporated to give 3.74 g (94%) of a pale yellow oil. LR-ES (C13H22O4): 243 (M+H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashed with acetone (10 mL)
  3. customevaporated to dryness to a white solid
  4. customThe residue was triturated with a mixture of 1:1 ether
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d27e67b3828a4671b910f645e78f6002
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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