Benzaldehyde, 4-ethyl-2-hydroxy- (9CI)

Benzaldehyde, 4-ethyl-2-hydroxy- (9CI) Property

Boiling point:

247.3±20.0 °C(Predicted)

Density 

1.134±0.06 g/cm3(Predicted)

storage temp. 

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

pka

8.27±0.10(Predicted)

Appearance

Light yellow to yellow Liquid

Safety

HS Code 

2914500090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Benzaldehyde, 4-ethyl-2-hydroxy- (9CI) Chemical Properties,Usage,Production

Synthesis

To a solution of 3-ethylphenol (6.11 g, 50 mmol) was sequentially added titanium (IV) chloride (100 ml, 100 mmol, 1 M solution in dichloromethane) and 1,1-dichlorodimethyl ether (7.47 ml, 82.5 mmol) at 0 °C. The reaction mixture was stirred at 0°C for 45 minutes. After completion of the reaction, the mixture was poured into ice water and extracted with ethyl acetate (EtOAc). The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a bright pink oil. Purification by fast column chromatography (eluent: hexane/ethyl acetate, 0 to 10% gradient) afforded 4-ethyl-2-hydroxybenzaldehyde (4.9 g, 65% yield) by first elution, followed by 2-ethyl-4-hydroxybenzaldehyde (1.32 g, 18% yield) by subsequent elution. 1H NMR (400 MHz, CDCl3) data of product A: δ 1.25 (t, J=7.6 Hz, 3H), 2.67 (d, J=7.6 Hz, 2H), 6.82 (s, 1H), 6.85 (d, J=8.0 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 9.83 (s, 1H), 11.05 (s, 1H). 1H NMR (400 MHz, CDCl3) data of product B: δ 1.27 (t, J=7.6Hz, 3H), 3.03 (d, J=7.6Hz, 2H), 6.68 (s, 1H), 6.78 (s, 1H), 6.82 (d, J=8.3Hz, 1H), 7.77 (t, J=8.3Hz, 1H), 10.10 (s, 1H).

References

[1] Patent: WO2006/18725, 2006, A1. Location in patent: Page/Page column 120-121