Toluene → 2-Acetoxycyclohex-3-enecarboxylic acid butyl ester

HRID 723521Notes

Reaction equation

HRID 723521 reaction equation
[C:1]([O:4][CH:5]=[CH:6][CH:7]=[CH2:8])(=[O:3])[CH3:2].[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])[CH:10]=C.[C:18]1(C)C=CC=CC=1>C1(C=CC(O)=CC=1)O>[CH2:5]([O:4][C:1]([CH:2]1[CH2:18][CH2:17][CH:16]=[CH:15][CH:14]1[O:13][C:9](=[O:12])[CH3:10])=[O:3])[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 8846Butyl AcrylateHCID 151951,3-Butadienyl acetate2×

Product 1

HCID 587439042-Acetoxycyclohex-3-enecarboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 785HydroquinoneCatalyst

Conditions

Temperature
120 °C

Procedure

1-Acetoxy-1,3-butadiene (30.1 g, 0.268 mol) was dissolved in toluene (20 mL). To this was added butyl acrylate (37.9 mL, 0.265 mol) and hydroquinone (0.14 g). The colourless solution was heated at 120° C. for 26 h under argon. More 1-acetoxy-1,3-butadiene (10.6 g, 0.095 mol) in toluene (2 mL) was then added, and heating continued for a further 68 h. The solution was cooled then evaporated in vacuo to give a viscous yellow oil (69 g), which was used without further purification.

Workup

  1. temperatureheating
  2. temperatureThe solution was cooled
  3. customthen evaporated in vacuo

Sources & evidence

ORD record
ord-912cb867b6b243ef9cdbe046b895fea0
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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