Hydrochloric Acid → 5-Iodo-2,4-dimethoxybenzaldehyde

HRID 347355Notes

Reaction equation

HRID 347355 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[I:13]Cl.Cl>CO>[I:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:7]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24640Iodine chlorideHCID 691752,4-Dimethoxybenzaldehyde

Product 1

HCID 142459555-Iodo-2,4-dimethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ex-35B: To a solution of 2.4-dimethoxybenzaldehye (20.0 g, 120.4 mmol) in methanol (550 mL) was added iodine monochloride (23.5 g in 60 mL methanol) dropwise over 20 min at ambient temperature. The solution was allowed to stir at this temperature. HPLC showed about 94% conversion after 3 hours. The reaction mixture was then poured into a solution of HCl (0.5M, 600 mL). The precipitate was collected by filtration, washed with water, dried in vacuo (40° C.) to give crude product of 33.02 g. The crude product was further purified by recrystallization from THF/heptane (1:1) to give 5-iodo-2,4-dimethoxybenzaldehyde as an off-white solid (27.5 g, m.p 170–172° C.). The mother liquid was concentrated to dryness. The residual material was dissolved in EtOH (100 mL) and acetone (20 mL) followed by addition of water (20 mL) to give additional product (3.12 g, m.p. 169–171° C.). Overall isolated yield of this reaction was 87.5%. 1H NMR (CDCl3) δ 10.20 (s, 1H), 8.22 (s, 1H), 6.39 (s, 1H), 3.97 (s, 3H), 3.95 (s, 3H). HRMS Calcd. for C9H9IO3: 291.9596 (M+); Found: 291.9602. Anal. Calcd. for C8H9NO3S: C, 37.01; H, 3.11; 1, 43.33; Found: C, 37.12; H, 3.15; I, 43.33.

Workup

  1. customafter 3 hours
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo (40° C.)
  5. customto give crude product of 33.02 g
  6. customThe crude product was further purified by recrystallization from THF/heptane (1:1)

Sources & evidence

ORD record
ord-c0fbe5a9cb7740ada998e0535174685e
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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