2,3-Dimethyl-1,3-butadiene → Dimethyl 4,5-dimethyl-1,4-cyclohexadiene-1,2-dicarboxylate

HRID 128766

Reaction equation

HRID 128766 reaction equation
[CH3:1][C:2]([C:4]([CH3:6])=[CH2:5])=[CH2:3].[C:7]([C:13]([O:15][CH3:16])=[O:14])#[C:8][C:9]([O:11][CH3:12])=[O:10]>O>[CH3:3][C:2]1[CH2:1][C:7]([C:13]([O:15][CH3:16])=[O:14])=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][C:4]=1[CH3:6]

Participants

4

Reactant 2

HCID 105662,3-Dimethyl-1,3-butadieneHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 600973Dimethyl 4,5-dimethyl-1,4-cyclohexadiene-1,2-dicarboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,3-dimethylbutadiene (9.84 g, 0.12 mol) and dimethyl acetylenedicarboxylate (14.29, 0.1 mol) were stirred together in water (50 ml) at 60° C. for 24 hours. The emulsion was cooled to room temperature and filtered. The filtered solid was recrystallised from diethyl ether to give the title compound In 78% yield. N.m.r: δH (90 MHz, CDCl3) 3.70 (s,6H), 1.71 ppm (s,6H)

Workup

  1. filtrationfiltered
  2. customThe filtered solid was recrystallised from diethyl ether

Sources & evidence

ORD record
ord-d941b562e9e741e18993d315dafbeac5
Source dataset
uspto-grants-1995_11
Patent number
US05464873

Linked notes

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