Water → (E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

Temperature

0 °C

Geraniol [1] (7.711 g, 50 mmol) and pyridine (3.955 g, 50 mmol) were suspended in anhydrous dichloromethane (200 ml) and chilled to 0° C. under an atmosphere of dry nitrogen. Chloroacetylchloride (5.647 g, 50 mmol) was added dropwise (violent reaction) and the resulting solution was stirred for 24 hrs at room temperature. Water (100 ml) was added, the organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic layers were successively washed with 2N HCl, saturated NaHCO3 solution and brine, dried over MgSO4 and the solvent was evaporated. Remaining volatile material was removed under reduced pressure (0.01 mbar) to yield product [2] as yellow liquid. The product was pure according to 1H NMR and directly subjected to the next step without further purification.

1. custom(violent reaction)
2. customthe organic layer was separated
3. extractionthe aqueous layer extracted with dichloromethane
4. washThe combined organic layers were successively washed with 2N HCl, saturated NaHCO3 solution and brine
5. dry with materialdried over MgSO4
6. customthe solvent was evaporated
7. customwas removed under reduced pressure (0.01 mbar)

ORD record

ord-22a5ea835527400ca78cd04294bdb569

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278134B2