Hydroquinone → Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

HRID 1992245Notes

Reaction equation

HRID 1992245 reaction equation
[CH2:1]1[CH:5]2[CH:6]3C=CC([CH:4]2C=[CH:2]1)C3.[CH3:11][O:12][C:13](=[O:16])[CH:14]=[CH2:15].C1(C=CC(O)=CC=1)O>>[CH3:11][O:12][C:13]([CH:14]1[CH2:4][CH:5]2[CH2:6][CH:15]1[CH:2]=[CH:1]2)=[O:16]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 6492DicyclopentadieneHCID 7294Methyl Acrylate

Product 1

HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylateYield 57.6%

Conditions

Temperature
220 °C

Procedure

Dicyclopentadiene (DCPD, available from Aldrich, 256.5 mL, 1.9 mol), methylacrylate (available from Aldrich, 405 mL, 4.5 mol) and hydroquinone (3.2 g, 0.03 mol) were charged into a 2 L high pressure reactor and heated to 220° C. The mixture was stirred at 300 rpm for 5 hours. After the reaction was completed, the resultant was cooled and transferred to a distiller. Vacuum distillation was carried out at 50° C. using a vacuum pump at 1 torr to obtain the product (yield: 57.6%, exo/endo=58/42).

Workup

  1. temperaturethe resultant was cooled
  2. distillationVacuum distillation
  3. customwas carried out at 50° C.
  4. customto obtain the product (yield: 57.6%, exo/endo=58/42)

Sources & evidence

ORD record
ord-6ffc389b81134a8da9f66565bb3c6e41
Source dataset
uspto-grants-2010_01
Patent number
US07648937B2

Reaction notes

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