Tetrahydrofuran → 1,5-Dimethoxy-1,4-cyclohexadiene

A solution containing 1,3-dimethoxybenzene (10 g), dry THF (15 mL) and tBuOH (15 mL) was added to distilled ammonia (ca 250 mL). To the reaction mixture was added lithium wire (1.5 g) in small portions, and the deep blue colored solution was stirred for 3 hours. The reaction mixture was decolorized by dropwise addition of methanol. Ammonia was evaporated at room temperature. To the residue, ammonium chloride solution was added, then the product was extracted with hexane (3×120 mL). The combined extracts were washed with water and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure gave the title compound as a clear liquid (9.5 g). 1H NMR (CDCl3): δ 2.7–2.9 (m, 4H, 2×CH2), 3.58 (s, 6H, 2×OCH3), 4.66 (t, 2H, olefinic).

1. additionwas added
2. distillationto distilled ammonia (ca 250 mL)
3. additionTo the reaction mixture was added lithium wire (1.5 g) in small portions
4. additionThe reaction mixture was decolorized by dropwise addition of methanol
5. customAmmonia was evaporated at room temperature
6. additionTo the residue, ammonium chloride solution was added
7. extractionthe product was extracted with hexane (3×120 mL)
8. washThe combined extracts were washed with water
9. dry with materialdried over anhydrous sodium sulfate
10. customRemoval of the solvent under reduced pressure

ORD record

ord-c6cd8c8908e24233bb3bdec932878a9d

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982260B1