M-Cresol → 3-(methoxymethoxy)toluene

Temperature

0 °C

Part A. Sodium hydride dispersion in mineral oil (5.05 g, 50% w/w, 105 mmol) was washed with hexane and dried under vacuum. DMF (100 mL) was added, the slurry was cooled to 0° C., and treated with a solution of m-cresol (10 mL, 95.6 mmol) in DMF (20 mL). The resulting mixture was allowed to stir for 1 h, then was treated with chloromethyl methyl ether (8.00 mL, 105 mmol) by syringe. The mixture was stirred overnight, then poured into ethyl acetate (200 mL). This was washed with water (3×200 mL) and brine (100 mL), and the aqueous phases were back-extracted in sequence with ethyl acetate. The extracts were combined, dried over magnesium sulfate, filtered and evaporated. The oily product was purified by elution through a plug of silica gel with 10:90 ethyl acetate-hexane. Evaporation then afforded the pure product, 3-(methoxymethoxy)toluene, as an oil (13.93 g, 91.5 mmol, 96%). TLC RF 0.46 (10:90 ethyl acetate-hexane). 1H NMR (300 MHz, CDCl3): d 7.17 (1H, t, J=7.7 Hz), 6.86-6.81 (3H, m), 5.17 (2H, s), 3.48 (3H, s), 2.33 (3H, s). MS (H2O-GC/Ms): m/e 153 (60), 121 (100).

1. washSodium hydride dispersion in mineral oil (5.05 g, 50% w/w, 105 mmol) was washed with hexane
2. customdried under vacuum
3. additionDMF (100 mL) was added
4. stirringThe mixture was stirred overnight
5. washThis was washed with water (3×200 mL) and brine (100 mL)
6. extractionthe aqueous phases were back-extracted in sequence with ethyl acetate
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. customevaporated
10. customThe oily product was purified by elution through a plug of silica gel with 10:90 ethyl acetate-hexane
11. customEvaporation

ORD record

ord-54f3c73f37264e2db834817be43a7150

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362180B1