4-Hydroxybenzaldehyde → Octanoic acid, 4-formylphenyl ester

To a 250 mL dry round bottom flask were added 4-hydroxybenzaldehyde (6.11 g, 50.0 mmol) and anhydrous CH2Cl2 (50 mL). The solution was cooled in an ice-water bath, then pyridine (8.09 mL, 100 mmol) was added. To the resulting solution, octanoyl chloride (10.3 mL, 60 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 (100 mL) was added and the CH2Cl2 layer was separated. The aqueous layer was extracted continually with CH2Cl2 (100 mL×2). 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 4-formylphenyl octanoate (10.7 g) as colorless oil. Yield: 86%. 1H NMR (CDCl3, 300 MHz): δ=9.98 (s, 1H), 7.91 (d, J=8.7 Hz, 2H), 7.26 (d, J=8.4 Hz, 2H), 2.58 (t, J=6.9 Hz, 2H), 1.38-0.86 (m, 13H). 13C NMR (CDCl3, 75.5 MHz): δ=191.0, 171.7, 155.6, 134.0, 131.3, 122.5, 34.5, 31.7, 29.1, 29.0, 24.9, 22.7, 14.2.

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 (100 mL×2)
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-58f6120f08804cfbbbc5c7fea7fdeef8

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822435B2