1,1-Dichloroethane → HCID 69516703, compound

Temperature

0 °C

In a three neck round bottom flask equipped with a reflux condenser and stir bar under N2 atmosphere was added finely pulverized aluminum trichloride (8.7 g, 65.2 mmol) to dichloroethane (22 mL). The solution was chilled to 0° C. Propionyl chloride was added dropwise 4.9 mL (57 mmol)and the mixture was stirred vigorously for 10 min. 4-Chloro-2-methoxy-1-methyl-benzene (8.5 g, 54.3 mmol) was then added dropwise with cooling to maintain internal solution temperature below 20° C. For less reactive aromatic rings the arene itself was used as solvent. The mixture was stirred for one hour with gradual warming to room temperature, then heated to 50° C. overnight. When starting material was not visible by TLC the reaction was cooled to room temperature. The reaction was quenched by pouring into ice and the layers separated in a separatory funnel. The aqueous phase was extracted once with chloroform. The combined organic layers were washed with 10 N HCl, water, aqueous NaHCO3 (saturated) then dried (sodium sulfate), and concentrated in vacuo. The product was then purified by chromatography on silica using an ethyl acetate/hexane gradient. Yield: 5.41 g white crystalls (51%). 1H NMR (300 MHz, CDCl3) •1.28 (t, CH3, 3H, J=7.0 Hz), 2.27 (s, CH3, 3H), 3.06 (q, CH2, 2H, J=7.0 Hz) 3.95 (s, —OCH3, 3 H), 6.91 (s, Ar, 1H, ), 6.95 (s, Ar, 1H), 7.50 (s, Ar, 1H).

1. customIn a three neck round bottom flask equipped with a reflux condenser
2. stirringthe mixture was stirred vigorously for 10 min
3. temperaturewith cooling
4. temperatureto maintain internal solution temperature below 20° C
5. stirringThe mixture was stirred for one hour
6. temperaturewith gradual warming to room temperature
7. temperatureheated to 50° C. overnight
8. temperaturewas cooled to room temperature
9. customThe reaction was quenched
10. additionby pouring into ice
11. customthe layers separated in a separatory funnel
12. extractionThe aqueous phase was extracted once with chloroform
13. washThe combined organic layers were washed with 10 N HCl, water, aqueous NaHCO3 (saturated)
14. dry with materialthen dried (sodium sulfate)
15. concentrationconcentrated in vacuo
16. customThe product was then purified by chromatography on silica using an ethyl acetate/hexane gradient

ORD record

ord-012700d147b445678ff00e778098a894

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07276526B2