4-Hydroxybenzaldehyde → 3-Chloro-4-hydroxybenzaldehyde

To a stirred solution of 4-hydroxybenzaldehyde (5.0 g, 40.0 mmol) in DCM (50 mL) SOCl2 (3.30 mL, 40.0 mmol) was added slowly at 0° C. After the addition was completed, the reaction mixture was brought to RT and stirred for 14 h. The reaction mixture was then quenched with water (50 mL), neutralized with a saturated NaHCO3 solution and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to obtain crude product. The crude material was purified via silica gel column chromatography to afford 3-chloro-4-hydroxybenzaldehyde (5.0 g, 77%) as a brown solid.

1. additionAfter the addition
2. customwas brought to RT
3. customThe reaction mixture was then quenched with water (50 mL)
4. extractionextracted with EtOAc (2×100 mL)
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto obtain crude product
10. customThe crude material was purified via silica gel column chromatography

ORD record

ord-104d9896b2ac46bcb8d6067f35595066

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071595B2