Tetrahydrofuran → Acetone cyclohexane
Reaction equation
N[CH2:2]/[CH:3]=[CH:4]/[CH:5]=[CH2:6].[CH2:7]1[CH2:11][O:10]CC1>>[CH2:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:2][C:11]([CH3:7])=[O:10]Participants
Procedure
Initially introduce 83.2 g (1.0 mol) of (E)-1-amino-2,4-pentadiene (title compound from Example B.2.) in 250 ml of THF, and add 0.1 g of 4-hydroxyanisole. Subsequently, at an internal temperature of 20°-30° C., add 229.2 g (1.05 mol) of di-tert-butyl dicarbonate dissolved in 250 ml of THF dropwise. After addition is complete, stir at room temperature for 20 h. Add 103.0 g (1.05 mol) of maleic anhydride, and heat to reflux for 5 h. Concentrate and take up the residue in 500 ml of methanol, add 30 ml of p-toluenesulphonic acid, and then heat once again to reflux for 5 h. After cooling with ice, and stirring, rapidly add a solution of 20 g of sodium carbonate dissolved in 500 ml of water dropwise, allow the mixture to stand for a further 30 min in an ice bath, and filter off the precipitate with suction, wash it with a little water, and dry it at 50° C. to constant weight.
Sources & evidence
- ORD record
- ord-d39e456c66464de298b2474cf2552cc5
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556979
Reaction notes
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