Barium hydroxide → 6-Methoxycarbonyl-1-carboxy-3-hexyne

HRID 1612987

Reaction equation

HRID 1612987 reaction equation
[C:1]([CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][C:11]([O:13]C)=[O:12])([O:3][CH3:4])=[O:2].[OH-].[Ba+2].[OH-]>CO>[CH3:4][O:3][C:1]([CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:2]

Participants

4

Reactant 2

HCID 6093286Barium hydroxideHCID 109545171,6-Dicarbomethoxy-3-hexyne

Product 1

HCID 109761516-Methoxycarbonyl-1-carboxy-3-hexyneYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

1,6-Dicarbomethoxy-3-hexyne (20.0 g, content; 83.9 0.0847 mole) is dissolved in methanol (40 g) and the mixture is cooled to 5° C. To the mixture is added 2 N anhydrous barium hydroxide (33.9 g) and the mixture is stirred. After stirring for 17 hours, the reaction mixture is filtered, and dried under reduced pressure. The resulting crystal is suspended in 1,2-dichloroethane (100 g) and thereto are added 10 % hydrochloric acid (16 g) and water (50 g). The reaction temperature is raised to 40°-45° C., and the mixture is stirred for 2 hours and then separated. The organic layer is washed with water (50 g) and concentrated under reduced pressure to give 6-methoxycarbonyl-1-carboxy-3-hexyne [VI-1] (12.5 g, yield; 80.2%),

Workup

  1. stirringAfter stirring for 17 hours
  2. filtrationthe reaction mixture is filtered
  3. customdried under reduced pressure
  4. additionare added 10 % hydrochloric acid (16 g) and water (50 g)
  5. temperatureThe reaction temperature is raised to 40°-45° C.
  6. stirringthe mixture is stirred for 2 hours
  7. customseparated
  8. washThe organic layer is washed with water (50 g)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbe349e56a4748c0a1751b4eb64eaa76
Source dataset
uspto-grants-1993_03
Patent number
US05191109

Linked notes

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