1,3-Butadiene → HCID 14484448, compound

HRID 1586899Notes

Reaction equation

HRID 1586899 reaction equation
[C:1]([O:4][CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2].[CH2:12]=[CH:13][CH:14]=[CH2:15]>C1(C)C=CC=CC=1>[C:1]([O:4][C@@H:5]1[CH2:15][CH:14]=[CH:13][CH2:12][C@H:6]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 3047722Ethyl 3-(acetyloxy)-2-propenoate

Product 1

HCID 14484448HCID 14484448, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
170 °C

Procedure

Ethyl 3-acetoxyacrylate (1, 11.0 g, 69.6 mmol) and butadiene (30.0 ml, 0.8 mol) were dissolved in toluene (distilled from calcium hydride, 25 ml); the mixture was placed in a 500 ml autoclave at -78° C. The autoclave was sealed, and then heated for 15 hours at 170° C. The autoclave was cooled and opened, the contents centrifuged, and the gummy residue extracted with toluene (3×100 ml). The toluene was removed under vacuum, and the mixture of cis and trans 1-acetoxy-2-carboethoxycyclohex-4-ene (3 and 2) was isolated by distillation (101° C. at 2 torr).

Workup

  1. customwas placed in a 500 ml autoclave at -78° C
  2. customThe autoclave was sealed
  3. temperatureThe autoclave was cooled
  4. extractionthe gummy residue extracted with toluene (3×100 ml)
  5. customThe toluene was removed under vacuum
  6. additionthe mixture of cis

Sources & evidence

ORD record
ord-18fc8da56acb4e8392b528b8d14463c5
Source dataset
uspto-grants-1993_06
Patent number
US05216141

Reaction notes

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