Methyl iodide → 1-(4-Chloro-2-methoxyphenyl)ethan-1-one

Temperature

0 °C

A solution of 4'-chloro-2'-hydroxyacetophenone (1.0 g) in dry DMF (5 ml) was added to a stirred mixture of sodium hydride (0.235 g, 60% dispersion) in dry DMF (5 ml) at 5° C. under nitrogen. After the addition the mixture was stirred at 0° C. for 15 minutes and then at ambient temperature for 1 hour. A solution of iodomethane (0.92 g) in dry DMF (5 ml) was added dropwise to the mixture whilst keeping the temperature below 10° C. The reaction mixture was stirred at ambient temperature for 5 hours and then left to stand for 16 hours. Potassium carbonate solution was added to basify the mixture and the product was extracted into dichloromethane. The combined extracts were dried and evaporated. The residue was dissolved in ether, washed with water, then dried and evaporated to give 4'-chloro-2'-methoxyacetophenone which was sufficiently pure for synthetic use in Example 17.

1. additionAfter the addition the mixture
2. waitat ambient temperature for 1 hour
3. customthe temperature below 10° C
4. stirringThe reaction mixture was stirred at ambient temperature for 5 hours
5. waitleft
6. waitto stand for 16 hours
7. extractionthe product was extracted into dichloromethane
8. customThe combined extracts were dried
9. customevaporated
10. dissolutionThe residue was dissolved in ether
11. washwashed with water
12. customdried
13. customevaporated

ORD record

ord-fb0c1353c9004e1cb2a480d18bb2a1e5

Source dataset

uspto-grants-1996_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05547972