Diethyl Ether → HCID 13133262, compound

To 0.30 g (2.26 mmoles) of AlCl3 in 50 mL of THF was added 2.1 mL of 2.09M EtMgCl in ether (4.40 mmoles). The aluminum reagent was added dropwise to 1.00 g (4.40 mmoles) of 2,3-DCNQ in 100 mL of THF and the mixture was stirred overnight. A homogeneous yellow solution was obtained. Then, 0.300 g (2.21 mmoles) of ZnCl2 was added and the mixture was stirred overnight. A white solid formed; the mixture was poured into 100 mL of NH4Cl solution and extracted with 3×50 mL of ether. The organic layer was dried over MgSO4, filtered and solvent was removed in vacuo. The residue was extracted with hexane, filtered and solvent was removed. The residue was chromatographed in silica gel eluted with toluene to give 0.39 g (1.77 mmole, 40%) of 2-ethyl-3-chloronaphthoquinone.

1. customA homogeneous yellow solution was obtained
2. stirringthe mixture was stirred overnight
3. customA white solid formed
4. extractionextracted with 3×50 mL of ether
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. customsolvent was removed in vacuo
8. extractionThe residue was extracted with hexane
9. filtrationfiltered
10. customsolvent was removed
11. customThe residue was chromatographed in silica gel
12. washeluted with toluene

ORD record

ord-d833b7c20ea54ff68c3704f488aefde8

Source dataset

uspto-grants-1985_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04507241