1-(3-Chlorophenyl)ethanone → 191014-74-1

Temperature

130 °C

A stirred mixture of 3'-Chloroacetophenone (15 mL, 97 mmol) and glyoxylic acid monohydrate (9 g, 97 mmol) was heated at 130° C. under reduced pressure (1,5 mmHg), over 8 hours. During this time the reduced pressure was maintained in order to remove the water formed during the reaction. After cooling, the crude reaction product was taken up in aqueous 10% potassium carbonate solution (100 mL) and the resulting solution was washed with diethyl ether (3×30 mL), the alkaline aqueous layer was cooled at 0° C. and then cautiously acidified with 6N HCl. The resulting suspension was extracted with ethyl acetate (3×50 mL), the collected organic extracts were washed with brine and dried (Na2SO4). Concentration of the solvent in vacuo afforded a yellow solid (8 g) which was chromatographed (SiO2 ;CH2Cl2 /MeOH 98:2) to provide the pure acid (6 g, 30%), lightly yellow solid melting at 158-59° C. (diisopropyl ether).

1. temperatureDuring this time the reduced pressure was maintained in order
2. customto remove the water
3. customformed during the reaction
4. temperatureAfter cooling
5. customthe crude reaction product
6. washthe resulting solution was washed with diethyl ether (3×30 mL)
7. temperaturethe alkaline aqueous layer was cooled at 0° C.
8. extractionThe resulting suspension was extracted with ethyl acetate (3×50 mL)
9. washthe collected organic extracts were washed with brine
10. dry with materialdried (Na2SO4)

ORD record

ord-3771ff92a6f64d87be275cef67f490d9

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06048896