Salicylaldehyde → HCID 10085569, compound

Temperature

130 °C

Quinaldine (2.84 mL, 3.00 g, 21.0 mmol, 1.0 eq.) and 2-hydroxybenzaldehyde (2.23 mL, 2.56 g, 21.0 mmol, 1.0 eq.) were dissolved in acetic anhydride (25 mL). The resulting mixture was heated at 130° C. for 16 h. The mixture was allowed to cool down to r.t. and was poured onto water (150 mL) and was stirred vigorously. The mixture was extracted with ethyl acetate (3×75 mL). The combined organic extracts were washed with saturated aqueous ammonium acetate (2×75 mL) and brine (75 mL), dried over sodium sulfate and concentrated under reduced pressure which gave the crude product as a red oil. The crude product was purified by column chromatography (SiO2, 1:4 ethyl acetate-cyclohexane) which yielded the product (5.88 g, 97% yield) as a clear yellow oil which crystallised upon standing.

1. temperatureto cool down to r.t.
2. additionwas poured onto water (150 mL)
3. extractionThe mixture was extracted with ethyl acetate (3×75 mL)
4. washThe combined organic extracts were washed with saturated aqueous ammonium acetate (2×75 mL) and brine (75 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure which
7. customgave the crude product as a red oil
8. customThe crude product was purified by column chromatography (SiO2, 1:4 ethyl acetate-cyclohexane) which

ORD record

ord-c37bb3d511374e3eaa5721bdedfd8613

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388138B2