Methanol → Methyl 5-formyl-2,4-dimethylbenzoate
Reaction equation
[CH:1]([C:3]1[C:4]([CH3:13])=[CH:5][C:6]([CH3:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])=[O:2].S(=O)(=O)(O)O.[CH3:19]O>>[CH:1]([C:3]1[C:4]([CH3:13])=[CH:5][C:6]([CH3:12])=[C:7]([CH:11]=1)[C:8]([O:10][CH3:19])=[O:9])=[O:2]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
Into a 250-mL round-bottom flask, was placed 5-formyl-2,4-dimethylbenzoic acid (compound 83.1, 2.00 g, 11.2 mmol) and methanol (50 mL). Concentrated sulfuric acid (2 mL) was carefully added drop-wise and the resulting solution was stirred for 2 h at 80° C., then cooled and the volatiles were removed under reduced pressure. The pH of the residue was adjusted to 9 with sodium bicarbonate (sat.), then the aqueous phase was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (2×20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 2.0 g (crude) of the title compound as yellow oil. The crude product was used in next step without further purification.
Workup
- customInto a 250-mL round-bottom flask, was placed
- temperaturecooled
- customthe volatiles were removed under reduced pressure
- extractionthe aqueous phase was extracted with ethyl acetate (3×50 mL)
- washThe combined organic layers were washed with brine (2×20 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-127f5fcb741645cca2390998263a80d2
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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