Trichloroacetyl chloride → 1,1-Dichlorospiro[3.5]nonan-2-one

This was prepared according to a literature procedure (Tetrahedron 1993, 49(36), 8159). Activated zinc (5.00 g; 76.5 mmol) (prepared according to Example 150, Step B) and methylenecyclohexane (2.40 g; 25.0 mmol) in dry ether (100 mL) under nitrogen were mixed in a 250 mL 3-neck flask with an addition funnel and condenser attached. The mixture was placed in a sonic bath at 25° C. Trichloroacetyl chloride (5.91 g; 32.5 mmol) in dry ether (50 mL) was added dropwise as the solution was sonicated. The sonication was continued for 3 hours. The mixture was filtered through Celite® and the solution was washed with saturated aqueous ammonium chloride solution (50 mL) and aqueous sodium bicarbonate solution (50 mL). The solution was dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was passed through a plug of silica gel using ether. The filtrate was evaporated to give the product as a yellow oil (5.03 g).

1. customThis was prepared
2. customThe mixture was placed in a sonic bath at 25° C
3. customwas sonicated
4. customThe sonication
5. filtrationThe mixture was filtered through Celite®
6. washthe solution was washed with saturated aqueous ammonium chloride solution (50 mL) and aqueous sodium bicarbonate solution (50 mL)
7. dry with materialThe solution was dried (sodium sulfate)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe filtrate was evaporated

ORD record

ord-3f43b7f425b344acbd5ef96e98b12228

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962596B2