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

HRID 1437313Notes

Reaction equation

HRID 1437313 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 hours 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 hours. 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-f3edd721696b4ef2b8722cd585b83fe5
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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