Acetone → 2,3,4-Trimethoxybenzyl iodide

HRID 1585344Notes

Reaction equation

HRID 1585344 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH2:5]Cl.CC(C)=O.[I-:19].[Na+]>CCOCC>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH2:5][I:19]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 97491Toluene, alpha-chloro-2,3,4-trimethoxy-

Product 1

HCID 212211282,3,4-Trimethoxybenzyl iodide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

46.64 g (215.2 mmol) of 2,3,4-trimethoxybenzyl chloride in 466 ml of abs. acetone are treated with 156.7 g (4.86 equivalents) of sodium iodide, and this mixture is stirred at RT for 2.75 h while excluding light. The reaction mixture is treated with approximately 3 l of (cold) ether, and the organic phase is washed once with 10% sodium thiophosphate solution and twice with saline (both kinds of solutions being cold). The combined aqueous phases are reextracted with ether. The combined organic phases are dried over Na2SO4 and evaporated on a RE, at approximately 30° C. The residue, which is the desired title compound, is dried again under HV and subjected to further processing as a crude product. 1H-NMR (200 MHz, CDCl3): 7.03 and 6.59 (each d; each 1H); 4.47 (s, 2H); 4.05, 3.85 and 3.84 (each s, each 3H).

Workup

  1. washthe organic phase is washed once with 10% sodium thiophosphate solution and twice with saline (both kinds of solutions
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. customevaporated on a RE, at approximately 30° C
  4. customis dried again under HV

Sources & evidence

ORD record
ord-3f1a6a1682ee406abe0813e747991687
Source dataset
uspto-grants-1999_08
Patent number
US05935976

Reaction notes

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