3-Chromanone

3-Chromanone Property

Boiling point:

195-205 °C(Press: 0.1-0.25 Torr)

Density 

1.196±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

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.

3-Chromanone Chemical Properties,Usage,Production

Synthesis Reference(s)

Synthesis, p. 268, 1984 DOI: 10.1055/s-1984-30805

Synthesis

General procedure for the synthesis of 3-dihydrochromanone from 2H-benzopyran-3-carboxylic acid: a toluene (24 mL) solution of DPPA (4.812 g, 17.494 mmol) was added slowly and dropwise to a mixed DCM (80 mL) and triethylamine (4.0 mL) of compound 2H-benzopyran-3-carboxylic acid (2.8 g, 15.9 mmol) in a room temperature solution. The reaction mixture was stirred at 50 °C for 1 h. Additional toluene (50 mL) was subsequently added. The reaction system was warmed to 85°C and heating was continued for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature, an aqueous 6.0N HCl solution (28 mL) was added, and the mixture was heated to reflux for 3 hours. At the end of the reaction, the organic layer was separated, washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/EtOAc = 10:0 to 7:3) to afford the target compound 3-dihydrochromanone (2.0 g, yield: 85%).1H NMR (400 MHz, CDCl3): δ 7.55-7.51 (m, 1H), 7.24-7.22 (m, 1H), 7.06-7.03 (m , 1H), 4.42 (s, 2H), 3.61 (s, 2H).

References

[1] Patent: WO2014/145512, 2014, A2. Location in patent: Page/Page column 116; 117
[2] European Journal of Organic Chemistry, 2001, # 22, p. 4207 - 4212
[3] Patent: US2008/153871, 2008, A1. Location in patent: Page/Page column 13
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 8, p. 2059 - 2063
[5] Angew. Chem., 2017, vol. 129, # 8, p. 2091 - 2095,5