Acetone → 2,3,4-Trimethoxybenzyl iodide

HRID 2394133Notes

Reaction equation

HRID 2394133 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-0d96320ce7314b32a91d4693e045ac3a
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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