Chloromethyl Methyl Ether → 1-Bromo-3-(tert-butyl)-2-(methoxymethoxy)-5-methylbenzene

Temperature

0 °C

Under nitrogen atmosphere, a THF 50 ml solution of 2-bromo-4-methyl-6-tert-butylphenol(23.41 g, 100 mmol) was added dropwise at 0° C. with stirring to a 100 ml THF suspension of sodium hydride (60%, 5.20 g, 130 mmol). After 2 hours, a THF 20 ml solution of methoxymethyl chloride (95%, 12.71 g, 150 mmol) was added dropwise to the mixture obtained above, the resulting mixture was brought up to room temperature and stirred for 10 hours. The reaction liquid thus obtained was cooled to 0° C., 100 ml of water was added thereto, and the aqueous layer was extracted with toluene (extracted twice with 200 ml of toluene). The organic solution layers were combined, washed with 100 ml of saturated aqueous sodium chloride solution, then dried with anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel column chromatography to obtain a colorless oil. The 1H-NMR spectrum data of the oil are shown below. The NMR data were determined by using EX-270 (mfd. by JEOL).

1. customobtained above
2. customwas brought up to room temperature
3. customThe reaction liquid
4. customthus obtained
5. extractionthe aqueous layer was extracted with toluene (
6. extractionextracted twice with 200 ml of toluene)
7. washwashed with 100 ml of saturated aqueous sodium chloride solution
8. dry with materialdried with anhydrous sodium sulfate
9. customthe solvent was removed
10. customThe residue was purified by silica gel column chromatography
11. customto obtain a colorless oil

ORD record

ord-1bd3af24a30f43e7b138e49457840870

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06066704