2,4,6-Trimethylpyridine → Neryl chloride

Temperature

0 °C

To a stirred solution of 10.0 g (64.83 mmol) of (Z)-3,7-dimethyl-2,6-octadien-1-ol and 9.42 mL (71.31 mmol) of 2,4,6-collidine under argon at room temperature was added dropwise 2.74 g (64.83 mmol) of lithium chloride in 30 mL of DMF. The mixture was cooled to 0° C. and treated with 5.52 mL (71.31 mmol) of methanesulfonyl chloride dropwise over 10 minutes. The reaction was stirred at 0° C. for 4 hours (solid present), then was poured into 300 mL of ice/water. The aqueous solution was washed three times with 200 mL portions of hexane. The organic layers were combined and washed with 5% KHSO4, water, saturated NaHCO3, brine, dried (MgSO4) and evaporated to provide 9.48 g (85%) of title chloride as a pale yellow oil.

1. washThe aqueous solution was washed three times with 200 mL portions of hexane
2. washwashed with 5% KHSO4, water, saturated NaHCO3, brine
3. dry with materialdried (MgSO4)
4. customevaporated

ORD record

ord-b1564ab221984964bfcee046024bb453

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05157027