tert-BUTYL CHLORIDE → 2,2,5,5-Tetramethyl-3-hexanone

2-chloro-2-methylpropane (75 g, 0.8 mol) was slowly added to magnesium pellets (19.5 g, 0.8 mol) in 800 mL of THF to make the Grignard reagent, tBuMgCl. This was added slowly to a mixture of cuprous chloride (49.5 g, 0.50 mol) and tertbutylacetylchloride (67.25 g, 0.50 mol), cooled to −50° C. in dry ice. After addition, the mixture was allowed to warm up to room temperature overnight. Most of the THF was removed by decreased pressure, followed by the addition of 500 mL of hexanes and 200 mL of 2M HCl. This mixture was filtered to remove the solid byproducts. The aqueous layer was washed 3× with 100 mL of hexanes, the hexanes layer washed 3× with 200 mL of 2M HCl, 2× with 200 mL of NaHCO3/water, 1× with 200 mL of water, and finally 1× with 200 mL of NaCl/water. The product mixture was then dried for an hour in MgSO4, which was subsequently removed by filtration. The hexane was then removed by atmospheric distillation.

1. additionAfter addition
2. customMost of the THF was removed
3. additionfollowed by the addition of 500 mL of hexanes and 200 mL of 2M HCl
4. filtrationThis mixture was filtered
5. customto remove the solid byproducts
6. washThe aqueous layer was washed 3× with 100 mL of hexanes
7. washthe hexanes layer washed 3× with 200 mL of 2M HCl, 2× with 200 mL of NaHCO3/water, 1× with 200 mL of water, and finally 1× with 200 mL of NaCl/water
8. dry with materialThe product mixture was then dried for an hour in MgSO4
9. customwhich was subsequently removed by filtration
10. customThe hexane was then removed by atmospheric distillation

ORDレコード

ord-2aaf5dbcffbe42a3bdfad3bf20802b35

出典データセット

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08703103B2