1-甲氧基-1,3-环己二烯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Reduction of anisole. Lithium, in small pieces, (8.75 g, 1.25 gram-atoms) was added to a solution of anisole (54 g, 0.5 mol) in n-propylamine (400 mL), ethylenediamine (105 g (1.75 mol) and t-butanol (111 g, 1.5 mol) cooled to -18°. The temperature increased to 12° and then decreased to -5°. After 2 hr all of the lithium had reacted and the reaction mixture was diluted with 800 mL of water added slowly. The mixture was extracted with ether (3×250 mL). The ether extracts were washed with water (3×200 mL) and brine (1×100 mL) and evaporated. The residue was distilled to give 27.5 g (50% of 1-methoxy-1,4-cyclohexadiene containing 10% of 1-methoxy-1,3-cyclohexadiene by glpc and nmr. cooled to -18° The temperature increased to 12° decreased to -5° added slowly The mixture was extracted with ether (3×250 mL) The ether extracts were washed with water (3×200 mL) and brine (1×100 mL) evaporated The residue was distilled

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1.08 g (7.2 mmol) of 2-propyl-1,4-benzoquinone and 2.20 g (20.0 mmol) of 1-methoxy-1,3-cylcohexadiene in 20 mL of benzene was heated at reflux for 2 h. The solution was concentrated in vacuo and the residue dried under high vacuum to afford a pale yellow oil. This material was dissolved in 20 mL of methanol and to that solution was added 1 mL of 2.0M HCl. The solution was stirred at room temperature for 6 hours, then was concentrated to about 5 mL volume. This was partitioned between ethyl acetate and water and the aqueous layer was washed with two portions of ethyl acetate. The organic extracts were sequentially washed with water and NaCl solution, combined, dried over magnesium sulfate, and concentrated. The residue was crystallized from ether-hexane to afford 0.764 g white crystals, 43%. at reflux for 2 h The solution was concentrated in vacuo the residue dried under high vacuum to afford a pale yellow oil was concentrated to about 5 mL volume This was partitioned between ethyl acetate and water the aqueous layer was washed with two portions of ethyl acetate The organic extracts were sequentially washed with water and NaCl solution dried over magnesium sulfate concentrated The residue was crystallized from ether-hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 0.57 g (5.0 mmol) of 2-methyl-1,4-benzoquinone and 1.10 g (10.0 mmol) of 1-methoxy-1,3-cylcohexadiene in 10 mL of benzene was heated at reflux for 2 h. The solution was concentrated in vacuo and the residue dried under high vacuum to afford a pale yellow oil. This material was dissolved in 15 mL of methanol and to that solution was added 1 mL of 2.0M HCl. The solution was stirred at room temperature for 6 hours, then was concentrated to about 5 mL volume. This was partitioned between ethyl acetate and water and the aqueous layer was washed with two portions of ethyl acetate. The organic extracts were sequentially washed with water and NaCl solution, combined, dried over magnesium sulfate, and concentrated. The residue was crystallized from ether-hexane to afford 0.452 g white crystals, 41%. at reflux for 2 h The solution was concentrated in vacuo the residue dried under high vacuum to afford a pale yellow oil was concentrated to about 5 mL volume This was partitioned between ethyl acetate and water the aqueous layer was washed with two portions of ethyl acetate The organic extracts were sequentially washed with water and NaCl solution dried over magnesium sulfate concentrated The residue was crystallized from ether-hexane