Sodium Iodide → Iodomethyl 3-methylbutyl carbonate

HRID 2295782Notes

Reaction equation

HRID 2295782 reaction equation
[C:1](=[O:11])([O:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])[O:2][CH2:3]Cl.[I-:12].[Na+]>CC(C)=O>[C:1](=[O:11])([O:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])[O:2][CH2:3][I:12]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 13269181Chloromethyl 3-methylbutyl carbonate

Product 1

HCID 20473993Iodomethyl 3-methylbutyl carbonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Chloromethyl isopentyl carbonate (4.2 g) was dissolved in dry acetone (25 ml) and anhydrous sodium iodide (6.0 g) was added to it. The reaction mixture was stirred at room temperature protected from light for 6 hours. The acetone was evaporated off. The residue was taken in water (50 ml) and extracted with ether. The ether extract was washed successively with aqueous sodium bisulfite, water and brine and dried over sodium sulfate. Evaporation of ether gave a light-yellow oil of product weighing 6.1 g NMR (CDCl3)δ 0.96 (6H, d, J=5 Hz, (CH3)2), 1.63 (3H, m, CH2CH), 4.26 (2H, t, J=7 Hz, OCH2) and 5.96 (2H, s, CH2I).

Workup

  1. customThe acetone was evaporated off
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed successively with aqueous sodium bisulfite, water and brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of ether
  7. customgave a light-yellow oil of product

Sources & evidence

ORD record
ord-6d4ce1e7e36e47f6956d09160b57dba4
Source dataset
uspto-grants-1984_01
Patent number
US04426391

Reaction notes

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