4-Bromotoluene → 2,2-Dimethyl-4-(4-methylphenyl)oxan-4-ol

Temperature

-78 °C

n-BuLi (26.3 ml, 1.6 M in hexane, 42 mmol) was added dropwise to a solution of 4-bromo-toluene (7.70 g, 45 mmol) in THF (100 ml) at −78° C. under N2. The resulting mixture was stirred at −78° C. for 30 min and a solution of tetrahydro-2,2-dimethyl-4H-pyran-4-one (3.84 g, 30 mmol) in THF (20 ml) was added. The resulting mixture was stirred at −78° C. for another 20 min and quenched by adding MeOH (10 ml). The reaction was concentrated under vacuum and the resulting residue was diluted with EtOAc (500 ml) and washed with sat. NH4Cl (250 ml), brine (250 ml), dried and concentrated to give 2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol as a white solid, which was used without further purification (5.41 g, 82%).

1. stirringThe resulting mixture was stirred at −78° C. for another 20 min
2. customquenched
3. additionby adding MeOH (10 ml)
4. concentrationThe reaction was concentrated under vacuum
5. additionthe resulting residue was diluted with EtOAc (500 ml)
6. washwashed with sat. NH4Cl (250 ml), brine (250 ml)
7. customdried
8. concentrationconcentrated

ORD record

ord-57934a96a31449408a013bd89323cc88

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08835488B2