4-Hydroxybenzaldehyde → 4-Hydroxy-3-iodobenzaldehyde

HRID 2370035Notes

Reaction equation

HRID 2370035 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[I:10]N1C(=O)CCC1=O>CC(O)=O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[I:10]

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 120273N-Iodosuccinimide

Product 1

HCID 9688814-Hydroxy-3-iodobenzaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 4-hydroxybenzaldehyde (2.0 g, 16.39 mmol) in AcOH (30 mL) was added N-iodosuccinimide (4.5 g, 19.67 mmol). The reaction mixture was stirred at r.t. for 16 h, then filtered. The filtrate was poured onto water (100 mL) and EtOAc (50 mL) was added. The aqueous fraction was separated, then extracted with EtOAc (3×50 mL). The combined organic fractions were washed with water (2×20 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (2.0 g, 50%) as a white solid that was used without further purification. LCMS (ES−) 247.1 (M−H)−, RT 1.44 minutes (Method 9).

Workup

  1. filtrationfiltered
  2. additionThe filtrate was poured onto water (100 mL) and EtOAc (50 mL)
  3. additionwas added
  4. customThe aqueous fraction was separated
  5. extractionextracted with EtOAc (3×50 mL)
  6. washThe combined organic fractions were washed with water (2×20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-359ccefcedad4950b91e31e19196ae3f
Source dataset
uspto-grants-2014_04
Patent number
US08710054B2

Reaction notes

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