Hydrochloric Acid → HCID 56653338, compound

HRID 2410198Notes

Reaction equation

HRID 2410198 reaction equation
[CH:1]([C:5]1[C:6]([OH:15])=[C:7]([CH:13]=[O:14])[CH:8]=[C:9]([CH:12]=1)[CH:10]=O)([CH2:3][CH3:4])[CH3:2].[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=1.Cl>O1CCOCC1>[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][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8500p-METHYLACETOPHENONEHCID 71545842HCID 71545842, compound

Product 1

HCID 56653338HCID 56653338, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-sec-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 conc.HCl (0.5 mL). The solution was heated at 80° C. for 2.5 h. Further, 0.5 mL of conc.HCl was added and reaction was continued for 2.5 h more. Most of the excess reagent was evaporated under reduced pressure, and the residue was suspended in water (50 mL) and 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-sec-butyl-2-hydroxy-5-(3-oxo-3-p-tolylprop-1-enyl)benzaldehyde (General Formula III).

Workup

  1. customreaction
  2. customMost of the excess reagent was evaporated under reduced pressure
  3. extractionextracted 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-b2d8e811afb04bcca252985c495734c1
Source dataset
uspto-grants-2014_08
Patent number
US08815940B2

Reaction notes

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