Methanol → HCID 90021077, compound

HRID 1487817Notes

Reaction equation

HRID 1487817 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:21]O>>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:21])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 900211532,4-Dimethyl-5-propionylbenzoic acid2×

Product 1

HCID 90021077HCID 90021077, compoundYield 70%

Conditions

Temperature
70 °C

Procedure

To a 100-mL round-bottom flask, was carefully added 2,4-dimethyl-5-propionylbenzoic acid (compound 1.4, 1.2 g, 5.8 mmol), sulfuric acid (1.0 mL, 19 mmol) and methanol (30 mL). The resulting solution was stirred at 70° C. for 5 h, then concentrated under reduced pressure. The residue was carefully diluted with H2O (50 mL) and extracted ethyl acetate (100 mL). The organic layer was washed with H2O (2×100 mL) and brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:100) as the eluent to yield the title compound as a light yellow solid (0.90 g, 70%).

Workup

  1. customTo a 100-mL round-bottom flask, was carefully added
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was carefully diluted with H2O (50 mL)
  4. extractionextracted ethyl acetate (100 mL)
  5. washThe organic layer was washed with H2O (2×100 mL) and brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:100) as the eluent

Sources & evidence

ORD record
ord-c6286a8bfd534bdfa8c9d774cf33948c
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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