2-Chlorotoluene → 2,2'-Dimethylbiphenyl

To a suspension of magnesium turnings (12.15 grams, 0.5 mole) in THF (150 mL) was added 2-chlorotoluene (50.6 grams, 0.40 mole). The mixture was refluxed for 18 hours, cooled to ambient and added dropwise to a solution of 2-chlorotoluene (44.3 grams, 0.35 mole) and bis(triphenylphosphine)-nickel (II) dichloride (2.0 grams) in THF (250 mL). The reaction mixture warmed upon mixing and was heated to reflux for 4 hours after completion of the addition. The reaction mixture was cooled and quenched by the addition of toluene (400 mL) and a saturated ammonium chloride solution (200 mL). The layers were separated and the organic phase was washed sequentially with 10 percent HCl (200 mL), water (3×100 mL), and then stripped under nitrogen to give a thick oil. The oil was distilled under vacuum to give the product as a fraction boiling in the range of 85° to 90° C. at 1 mm Hg. The yield was 43.40 grams (68 percent of theory) of 2,2'-dimethyl-1,1'-biphenyls containing 93 percent of the 2,2'-isomer and 3.5 percent of other isomers.

1. temperatureThe mixture was refluxed for 18 hours
2. temperaturecooled to ambient and
3. temperatureThe reaction mixture warmed
4. additionupon mixing
5. temperaturewas heated
6. temperatureto reflux for 4 hours
7. additionafter completion of the addition
8. temperatureThe reaction mixture was cooled
9. customquenched by the addition of toluene (400 mL)
10. customThe layers were separated
11. washthe organic phase was washed sequentially with 10 percent HCl (200 mL), water (3×100 mL)
12. customto give a thick oil
13. distillationThe oil was distilled under vacuum
14. customto give the product as a fraction
15. customboiling in the range of 85° to 90° C. at 1 mm Hg

ORDレコード

ord-9af3121319fc462384088d50a294a933

出典データセット

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05026886