Dimethyl Sulfide → 1-Chloro-3,7,11-trimethyldodeca-2,6,10-triene

Temperature

-30 °C

N-Chlorosuccinimide (0.66 g, 4.95 mmol) was dissolved in 20 ml of dry CH2Cl2 under a nitrogen atmosphere. The solution was cooled to -30° C. and 0.37 ml dimethyl sulphide (5 mmol) was added. The mixture was allowed to warm to 0° C. before it was cooled to -40° C. Then farnesol (1 g, 4.5 mmol) dissolved in 2.5 ml CH2 Cl2 was added dropwise to the mixture over a period of 3 minutes. The reaction mixture was warmed to 0.C in 1 h, at which temperature it was maintained for another hour. After 15 minutes of stirring at room temperature the reaction mixture was poured into a separatory funnel which contained 12.5 ml of cold saturated NaCl. The aqueous layer was extracted with two 10 ml portions of pentane. The organic layers were combined with an additional 10 ml of pentane and washed with two 5 ml portions of cold saturated NaCl. The organic layer was dried over MgSO4 and concentrated to dryness in vacuo. Compound (b) was thus obtained in a yield of 89%.

1. temperatureto warm to 0° C. before it
2. temperaturewas cooled to -40° C
3. additionwas added dropwise to the mixture over a period of 3 minutes
4. temperaturewas maintained for another hour
5. additionwas poured into a separatory funnel which
6. extractionThe aqueous layer was extracted with two 10 ml portions of pentane
7. washwashed with two 5 ml portions of cold saturated NaCl
8. dry with materialThe organic layer was dried over MgSO4
9. concentrationconcentrated to dryness in vacuo

ORD record

ord-635d70c0f4dc4421baad112495a628c2

Source dataset

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05827838