Ethyl (4-forMylphenyl)acetate

Ethyl (4-forMylphenyl)acetate Property

Boiling point:

300.6±17.0 °C(Predicted)

Density 

1.127±0.06 g/cm3(Predicted)

storage temp. 

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

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

Ethyl (4-forMylphenyl)acetate Chemical Properties,Usage,Production

Synthesis

GENERAL STEPS: To a screw-capped tube, 4-formylphenylboronic acid (450 mg, 3 mmol), ethyl bromoacetate (0.22 mL, 2 mmol), potassium carbonate (830 mg, 6 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 46 mg, 0.05 mmol), tris(1-naphthyl)phosphine (62 mg, 0.15 mmol), water (0.5 mL) and tetrahydrofuran (THF, 4.5 mL). The reaction mixture was degassed with nitrogen for 5 min and then the reaction was stirred at 65 °C in an oil bath for 18 h. The reaction was carried out in the presence of a nitrogen gas. After completion of the reaction, it was cooled to room temperature, diluted with ethyl acetate (50 mL) and washed with water (2 x 50 mL). The organic phase was filtered through a phase separator and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography eluting with a gradient of 0-20% ethyl acetate/isohexane solution to afford the target product ethyl 2-(4-formylphenyl) acetate as a colorless oil (327 mg, 57% yield).1H NMR (400 MHz, CDCl3) δ: 9.99 (s, 1H), 7.83 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 8.0 Hz, 2H), 4.19-4.12 (m, 2H), 3.70 (s, 2H), 1.28-1.20 (m, 3H).LCMS (Method 1): [MH+] = 193, retention time 3.58 min.

References

[1] Tetrahedron, 2010, vol. 66, # 42, p. 8238 - 8241
[2] Chemical Communications, 2001, # 7, p. 669 - 670
[3] Patent: WO2014/86852, 2014, A1. Location in patent: Page/Page column 67; 68
[4] Patent: US2014/155427, 2014, A1. Location in patent: Page/Page column