3-Hydroxybenzaldehyde → HCID 39199612, compound

To a 250 mL dry round bottom flask were added 3-hydroxybenzaldehyde (5.0 g, 41.0 mmol), anhydrous CH2Cl2 (50 mL). The solution was cooled in an ice-water bath, then pyridine (6.64 mL, 82.0 mmol) was added. To the resulting solution, butyryl chloride (5.15 mL, 49.2 mmol) was added slowly under stirring and N2. The mixture was first stirred at 0° C. for 2 hours, then at room temperature for 20 hours. To the reaction mixture, water (80 mL) was added and the CH2Cl2 layer was separated. The aqueous layer was extracted continually with CH2Cl2 (50 mL×3). The combined CH2Cl2 solution was dried over Na2SO4. After removal of the solvent, the residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting) to give 3-formylphenyl butyrate (5.9 g) as colorless oil. Yield: 75%. 1H NMR (CDCl3, 300 MHz): δ=9.96 (s, 1H), 7.72 (t of d, J=1.2, 7.5 Hz, 1H), 7.60 (t, J=2.4 Hz, 1H), 7.52 (t, J=8.1 Hz, 1H), 7.36-7.32 (m, 1H), 2.56 (t, J=7.5 Hz, 2H), 1.78 (sextet, J=7.2 Hz, 2H), 1.04 (t, J=7.5 Hz, 3H). 13C NMR (CDCl3, 75.5 MHz): δ=191.2, 171.7, 151.3, 137.7, 130.1, 127.8, 127.2, 122.2, 36.0, 18.3, 13.5.

1. customTo a 250 mL dry round bottom flask
2. temperatureThe solution was cooled in an ice-water bath
3. stirringThe mixture was first stirred at 0° C. for 2 hours
4. customthe CH2Cl2 layer was separated
5. extractionThe aqueous layer was extracted continually with CH2Cl2 (50 mL×3)
6. dry with materialThe combined CH2Cl2 solution was dried over Na2SO4
7. customAfter removal of the solvent
8. customthe residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting)

ORD record

ord-04615249e7254766b9c573786c5fc382

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822435B2