Benzaldehyde, 4-chloro-3-hydroxy- Chemical Properties

Melting point:

119-122°

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Yellow to brown Solid

Safety Information

HS Code 

2913000090

Benzaldehyde, 4-chloro-3-hydroxy- Usage And Synthesis

Uses

4-Chloro-3-hydroxybenzaldehyde can be used as a pharmaceutical synthesis intermediate.

Synthesis

3-Hydroxybenzaldehyde (1 g, 10 mmol) was used as starting material and dissolved in acetonitrile (50 mL). To this solution, p-toluenesulfonic acid was added in batches at room temperature and after stirring for 5 minutes, N-chlorosuccinimide (NCS, 1.33 g, 10 mmol) was added. The reaction mixture was continued to be stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction was quenched with aqueous sodium thiosulfate and subsequently diluted with ethyl acetate and brine. The organic layer was separated, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10:1 to 5:1) as eluent to afford 2-chloro-5-hydroxybenzaldehyde (340 mg, 21.7% yield, Intermediate 28a) and 4-chloro-3-hydroxybenzaldehyde (310 mg, 19.7% yield, Intermediate 28b) as yellow solids, respectively. 2-chloro-5-hydroxybenzaldehyde's 1H-NMR (CDCl3) data: δ 10.43 (s, 1H), 7.54-7.56 (d, 1H), 7.30-7.37 (m, 2H). 4-Chloro-3-hydroxybenzaldehyde 1H-NMR (CDCl3) data: δ 10.43 (s, 1H), 7.40 (d, 1H), 7.33 (d, 1H), 7.06- 7.09 (dd, 1H).

References

[1] Patent: WO2014/143799, 2014, A2. Location in patent: Page/Page column 391
[2] Patent: US2014/275528, 2014, A1. Location in patent: Paragraph 0322; 0323

Benzaldehyde, 4-chloro-3-hydroxy-(56962-12-0)Related Product Information

• 2,5-Dihydroxybenzaldehyde
• Salicylaldehyde
• Benzoyl chloride
• Benzyl alcohol
• Pyrrole
• Protocatechualdehyde
• Sodium hydroxide
• 4-Hydroxybenzoic acid
• 4-Hydroxybenzaldehyde
• 3-Hydroxybenzaldehyde