Methanol → 1,6-Dicarbomethoxy-3-hexyne
Reaction equation
Cl[CH2:2][C:3]#[C:4][CH2:5]Cl.[C:7]([O:13][CH3:14])(=[O:12])[CH2:8][C:9]([CH3:11])=O.[CH3:15][O-:16].[Na+].C[OH:19]>C1(C)C=CC=CC=1>[C:2]([CH2:3][CH2:4][C:5]#[C:11][CH2:9][CH2:8][C:7]([O:13][CH3:14])=[O:12])([O:16][CH3:15])=[O:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Toluene (796 g) is added to 1,4-dichloro-2-butyne (200 g, 1.63 mole), and to the mixture is added a mixture of methyl acetoacetate (568 g, 4.89 mole) and 28 % solution of sodium methylate in methanol (896 g, 4.65 mole) at room temperature. The reaction temperature is raised to 60° C., and the mixture is stirred for 16 hours. After completion of the reaction, the mixture is concentrated under reduced pressure, and methanol is removed therefrom. Water (1.5 liter) and toluene (1 liter) are added to the resulting residue, and the mixture is stirred. The aqueous layer is removed, and the toluene layer is washed with water (1.5 liter). The toluene layer is concentrated under reduced pressure, and further evaporated under reduced pressure to give 1,6-dicarbomethoxy-3-hexyne (109.7 g, content; 95.8%).
Workup
- additionto the mixture is added
- customAfter completion of the reaction
- concentrationthe mixture is concentrated under reduced pressure, and methanol
- customis removed
- additionWater (1.5 liter) and toluene (1 liter) are added to the resulting residue
- stirringthe mixture is stirred
- customThe aqueous layer is removed
- washthe toluene layer is washed with water (1.5 liter)
- concentrationThe toluene layer is concentrated under reduced pressure
- customfurther evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-c454e10cfe83435a9a783971773746c2
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05191109
Reaction notes
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