2-Tert-Butylphenol → HCID 57486422, compound

Temperature

0 °C

In dry tetrahydrofuran (25 mL) was suspended 4.80 g (120 mmol) of 60% sodium hydride, and a dry tetrahydrofuran (80 mL) solution containing 15.0 g (100 mmol) of 2-tert-butylphenol was added dropwise to this suspension at 0° C. After stirring the mixture at 0° C. for 10 minutes, a dry tetrahydrofuran (80 mL) solution containing 14.9 g (119 mmol) of 2-methoxyethoxymethyl chloride was added dropwise to the mixture. The reaction mixture was stirred in an ice bath for 4 hours and 30 minutes, and allowed to stand at room temperature overnight. To the reaction mixture were further added 1.20 g (30 mmol) of 60% sodium hydride and 3.8 g (30 mmol) of 2-methoxyethoxymethyl chloride at 0° C., and the mixture was stirred at 0° C. for 7 hours. The reaction mixture was poured into ice-cold water (250 mL), and extracted with ethyl acetate. The organic layers were combined, washed with 2N aqueous sodium hydroxide solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=20:1) to obtain 19.7 g (82.8 mmol, Yield: 82.8%) of tert-butyl-2-[(2-methoxyethoxy)methoxy]benzene.

1. additionwas added dropwise to this suspension at 0° C
2. additionwas added dropwise to the mixture
3. stirringThe reaction mixture was stirred in an ice bath for 4 hours and 30 minutes
4. waitto stand at room temperature overnight
5. customat 0° C.
6. stirringthe mixture was stirred at 0° C. for 7 hours
7. extractionextracted with ethyl acetate
8. washwashed with 2N aqueous sodium hydroxide solution and brine
9. dry with materialdried over anhydrous sodium sulfate
10. customThe solvent was removed
11. customthe residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=20:1)

ORD record

ord-917ccc62768446d995c452e18a0ad0e8

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608563B2