Benzene → (1-Methylcyclohexyl)benzene

Temperature

0 °C

A mixed solution of 75.0 mL (632 mmol) of 1-methyl-1-cyclohexene and 56.4 mL (632 mmol) of benzene was added dropwise to 225.6 mL (2.53 mol) of a benzene solution of 231 g (2.36 mol) of sulfuric acid at 0° C. over 1.5 hours. The resulting mixture was stirred at 0° C. for 1.5 hours. The reaction mixture was quenched with 300 mL of water to separate the aqueous layer. The resulting organic layer thus obtained was washed with 100 mL of a saturated aqueous solution of sodium bicarbonate, 100 mL of water, and 100 mL of saturated saline and dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated to obtain crude 1-methylcyclohexylbenzene. The resulting crude 1-methylcyclohexylbenzene was purified by distillation under reduced pressure (110 to 113° C./10 mmHg) to obtain 40.2 g of the intended product. Yield: 36.5%.

1. customThe reaction mixture was quenched with 300 mL of water
2. customto separate the aqueous layer
3. customThe resulting organic layer thus obtained
4. washwas washed with 100 mL of a saturated aqueous solution of sodium bicarbonate, 100 mL of water, and 100 mL of saturated saline
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationAfter the desiccant was filtered off
7. concentrationthe filtrate was concentrated
8. customto obtain crude 1-methylcyclohexylbenzene
9. distillationThe resulting crude 1-methylcyclohexylbenzene was purified by distillation under reduced pressure (110 to 113° C./10 mmHg)

ORD record

ord-5100c616d41b41d9ab7c298ced10f152

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09061959B2