Benzoyl Peroxide → 4-tert-Butyltoluene

Temperature

20 °C

N-Bromosuccinimide (98 g, 0.55 mol) and 0.5 g benzoyl peroxide were added to solution of 2-bromo-4-tert-butyl-1-methylbenzene (113.5 g, 0.5 mol) in CCl4 (500 ml). The resulting mixture was refluxed for 6 h, cooled to 20° C. and filtered. The resulting filtrate was evaporated and used without further purification. A solution of sodium diethylmethylmalonate, prepared from 104.5 g (0.6 mol) diethylmethylmalonate and 40.8 g of sodium ethylate in 500 ml abs. ethanol was treated dropwise with 2-bromo-1-(bromomethyl)-4-tert-butylbenzene (0.5 mol). The resulting mixture was refluxed for 4 h, treated with a solution of NaOH (50 g, 1.25 mol) in water (60 ml) and refluxed for 2 h, then poured into water (11), and finally washed with toluene (2×100 ml). The aqueous solution was treated with 130 ml of 35% HCl. The resulting mixture was extracted with chloroform (4×250 ml), the organic phase was dried over MgSO4 and evaporated. The residue was heated to 160-170° C. for 15 min yielding the product (92 g, total yield from 1-tert-butyl-4-methylbenzene 60%).

1. temperatureThe resulting mixture was refluxed for 6 h
2. filtrationfiltered
3. customThe resulting filtrate was evaporated
4. customused without further purification
5. temperatureThe resulting mixture was refluxed for 4 h
6. temperaturerefluxed for 2 h
7. washfinally washed with toluene (2×100 ml)
8. additionThe aqueous solution was treated with 130 ml of 35% HCl
9. extractionThe resulting mixture was extracted with chloroform (4×250 ml)
10. dry with materialthe organic phase was dried over MgSO4
11. customevaporated
12. temperatureThe residue was heated to 160-170° C. for 15 min
13. customyielding

ORD record

ord-20efc2e728e941e9a2c30c068d93dde9

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858717B2