Hydrochloric Acid → 4-tert-Butyl-2-hydroxybenzaldehyde

Temperature

0 °C

A solution of 5.69 g (30 mmol) of titan tetrachloride in 15 ml DCM were added dropwise at 0° C. under nitrogen to 3.76 g (25 mmol) of 3-tert-butylphenol dissolved in 75 ml DCM. After stirring for 30 min 3.16 g (27.5 mmol) of dichloromethyl methyl ether was added. The reaction mixture was stirred for 2 h at 0° C. Carefully 30 ml of 1N aqueous HCl solution and then 90 ml water were added. The reaction mixture was extracted twice with DCM. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (250 g silica gel, DCM) to yield 2.32 g (52%) 4-tert-butyl-2-hydroxy benzaldehyde as a light yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 10.62 (br s, 1H), 10.18 (s, 1H), 7.61 (d, 1H), 7.04 (d, 1H), 6.98 (s, 1H).

1. additionwas added
2. extractionThe reaction mixture was extracted twice with DCM
3. washThe combined organic layers were washed with saturated aqueous NaCl solution
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customthe solvent was evaporated
7. customThe residue was purified by column chromatography (250 g silica gel, DCM)

ORD record

ord-0758be2649754864b617cb53c8caed82

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259183B2