Iodine → HCID 56653338, compound

HRID 2410199Notes

Reaction equation

HRID 2410199 reaction equation
[C:1]([C:5]1[C:6]([OH:15])=[C:7]([CH:13]=[O:14])[CH:8]=[C:9]([CH:12]=1)[CH:10]=O)([CH3:4])([CH3:3])C.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=1.II.O1CCOC[CH2:29]1>>[CH:1]([C:5]1[C:6]([OH:15])=[C:7]([CH:8]=[C:9](/[CH:10]=[CH:24]/[C:23](=[O:25])[C:20]2[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=2)[CH:12]=1)[CH:13]=[O:14])([CH2:3][CH3:29])[CH3:4]

Participants

5

Reactant 4

HCID 807IodineHCID 8500p-METHYLACETOPHENONEHCID 312751,4-DioxaneHCID 3513573HCID 3513573, compound

Product 1

HCID 56653338HCID 56653338, compound

Conditions

Temperature
90 °C

Procedure

A solution of 5-tert-butyl-4-hydroxyisophthalaldehyde of formula I (0.50 g, 3.05 mmol) and p-methyl acetophenone (0.41 g, 3.05 mmol) in dioxane (25 mL) was treated with iodine (0.78 g, 0.31 mmol). The solution was heated at 90° C. for 5.0 h. Most of the excess reagent was evaporated under reduced pressure, and the residue was treated with aq. Na2S2O3 solution (5%, 40 mL) and the product was extracted 3-fold with CHCl3 (50 mL). The combined organic layers were dried on Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue was chromatographed over silica gel (SiO2, 230-400 flash), eluting with a gradient of 4% ethyl acetate in hexane, which upon concentration provides (E)-3-tort-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde (General Formula III).

Workup

  1. customMost of the excess reagent was evaporated under reduced pressure
  2. additionthe residue was treated with aq. Na2S2O3 solution (5%, 40 mL)
  3. extractionthe product was extracted 3-fold with CHCl3 (50 mL)
  4. customThe combined organic layers were dried on Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was chromatographed over silica gel (SiO2, 230-400 flash)
  8. washeluting with a gradient of 4% ethyl acetate in hexane, which upon concentration

Sources & evidence

ORD record
ord-1b686f938069488c865174a4377a241e
Source dataset
uspto-grants-2014_08
Patent number
US08815940B2

Reaction notes

Loading…