Dimethyl Sulfoxide → 3-Chloro-5,5-dimethyl-2,4-hexanedione

Chlorotrimethylsilane (26.8 ml, 0.21 mol) was added dropwise to a stirred pale yellow solution of tetrabutylammonium bromide (1.139, 3.50 mmol) in dry acetonitrile (100 ml) at room temperature under nitrogen. The resulting solution was cooled in ice and 5,5-dimethylhexane-2,4-dione (10.0 g, 70.4 mmol) and then dry dimethylsulphoxide (14.7 ml, 0.21 mol) were added dropwise over 5 minutes producing a yellow solution which was allowed to warm slowly to room temperature with stirring over 3 hours. The mixture was diluted with water (1000 ml) and stirred for 10 min and then extracted with ether (1×500 ml, 2×250 ml). The combined ether layers were dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a yellow oil. The crude product was purified by distillation under reduced pressure to provide the title compound (10.0 g) as a pale yellow oil, b.p. 220-225° C./60 mmHg.

1. temperatureThe resulting solution was cooled in ice
2. customproducing a yellow solution which
3. stirringstirred for 10 min
4. extractionextracted with ether (1×500 ml, 2×250 ml)
5. dry with materialThe combined ether layers were dried over magnesium sulphate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto leave a yellow oil
9. distillationThe crude product was purified by distillation under reduced pressure

ORD record

ord-203103d5af034b80b5a32f3b12f3ce19

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063044B2