Benzene → (1-Methylcyclobutyl)benzene

Temperature

0 °C

A stirred mixture of benzene (5.0 ml, 56 mmol) and Sulfuric acid (1.17 ml, 21.9 mmol) was cooled to 0° C. and treated dropwise with a solution of Methylenecyclobutane (1.00 ml, 10.8 mmol) in Benzene (3.0 ml, 34 mmol) over-1 h. Upon completion of the addition, the reaction mixture was stirred an additional 1 h while being warmed to RT. The mixture extracted with 15 ml of hexane. The organic phase was washed with 10 ml H2O and 10 ml sat NaHCO3, dried over Na2SO4, filtered and concentrated to yield a colorless liquid. The liquid was purified by kugelrohr distillation (5-10 torr) to yield the desired compound as a colourless liquid. First fraction was collected at 75-85° C. as a colorless liquid (330 mg) of product as a colorless liquid.

1. additionUpon completion of the addition
2. temperaturewhile being warmed to RT
3. extractionThe mixture extracted with 15 ml of hexane
4. washThe organic phase was washed with 10 ml H2O and 10 ml
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto yield a colorless liquid
9. distillationThe liquid was purified by kugelrohr distillation (5-10 torr)

ORD record

ord-0e67cce3de4241c88e58a5fb15ee372d

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096634B2