Iodine → HCID 23445631, compound

HRID 1871296Notes

Reaction equation

HRID 1871296 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].[OH-].[Na+].[I:13]I>CO>[I:13][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([CH3:10])[C:2]=1[OH:1])[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 23445631HCID 23445631, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 5° C., to a stirred solution containing commercial 4-hydroxy-3-methylbenzaldehyde (4.65 g, 34.1 mmol) and sodium hydroxide (2.73 g, 68.25 mmol) in MeOH (171 mL) was added iodine (10.8 g, 42.7 mmol). The reaction was stirred for 16 h, eventually warming to ambient temperature. The reaction was quenched with 1N HCl (200 mL) and extracted with ether. The ethereal extracts were washed with 10% Na2S2O3 (3×), with brine (3×), dried (MgSO4) and concentrated. Purification on Biotage KP-Sil eluting with 70% CH2Cl2 /pet. ether to give 7.28 g (81%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 2.30 (s, 3 H), 7.65 (d, J=1.02 Hz, 1 H), 8.09 (d, J=1.91 Hz, 1 H), 9.74 (s, 1 H), 10.25 (s, 1 H).

Workup

  1. customThe reaction was quenched with 1N HCl (200 mL)
  2. extractionextracted with ether
  3. washThe ethereal extracts were washed with 10% Na2S2O3 (3×), with brine (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification on Biotage KP-Sil
  7. washeluting with 70% CH2Cl2 /pet. ether

Sources & evidence

ORD record
ord-b00dcfd4614f41a2821ae3dfeee03a7c
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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