2-Tert-Butylphenol → 3-tert-Butyl-2-hydroxybenzaldehyde

2-tert-Butylphenol 7.51 g (50 mmol) and THF (tetrahydrofuran) 54 ml were charged in a sufficiently dried 500 ml reactor purged with argon, ethylmagnesium bromide 18.53 ml (an ether solution, 3.0N, 55.6 mmol) was added dropwise to the reactor at 0° C. in 15 minutes and after that, the temperature was gradually raised to a room temperature and the resultant mixture was stirred for 1 hour at a room temperature. Toluene 180 ml was added, the resultant mixture was heated to 100° C., and about 40 ml of the mixed solvents of ether and THF were evaporated off to obtain a slightly opaque slurry. After the slurry was cooled to a room temperature, p-formaldehyde 3.75 g (125 mmol) and triethylamine 10.45 ml (75 mmol) were added and the resultant mixture was stirred at 88° C. for 1 hour. After being cooled to a room temperature, the mixture was quenched with 10% hydrochloric acid and an organic layer was concentrated and purified by a silica gel column to obtain 3-tert-butylsalicylaldehyde 6.22 g (yield 70%).

1. custompurged with argon, ethylmagnesium bromide 18.53 ml (an ether solution, 3.0N, 55.6 mmol)
2. additionwas added dropwise to the reactor at 0° C. in 15 minutes
3. additionToluene 180 ml was added
4. temperaturethe resultant mixture was heated to 100° C.
5. customabout 40 ml of the mixed solvents of ether and THF were evaporated off
6. customto obtain a slightly opaque slurry
7. temperatureAfter the slurry was cooled to a room temperature
8. temperatureAfter being cooled to a room temperature
9. customthe mixture was quenched with 10% hydrochloric acid
10. concentrationan organic layer was concentrated
11. custompurified by a silica gel column

ORD record

ord-e91c3cf344c440ecb4edd2efa93a9cc9

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07563849B2