Hydroquinone → 5-Norbornene 2-allylacetate

HRID 1160022Notes

Reaction equation

HRID 1160022 reaction equation
C1[CH:5]2[C@@H:6]3[CH:10]=[CH:9][C@H:8]([CH:4]2C=C1)[CH2:7]3.[CH2:11]([CH2:14][C:15]([O-:17])=[O:16])[CH:12]=[CH2:13].C1(C=CC(O)=CC=1)O>>[CH:6]12[CH2:7][CH:8]([CH:4]=[CH:5]1)[CH2:9][CH2:10]2.[CH2:11]([CH2:14][C:15]([O-:17])=[O:16])[CH:12]=[CH2:13]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 50778374-PentenoateHCID 15618652endo-Dicyclopentadiene

Product 1

HCID 865975875-Norbornene 2-allylacetateYield 30%

Conditions

Temperature
190 °C

Procedure

DCPD (available from Aldrich, 248 mL, 1.852 mol), allylacetate (available from Aldrich, 500 mL, 4.63 mol) and hydroquinone (0.7 g, 0.006 mol) were charged into a 2 L high pressure reactor and heated to 190° 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 2 times at 56° C. using a vacuum pump at 1 torr to obtain the product (yield: 30%, exo/endo=57/43).

Workup

  1. temperaturethe resultant was cooled
  2. distillationVacuum distillation
  3. customat 56° C.
  4. customto obtain the product (yield: 30%, exo/endo=57/43)

Sources & evidence

ORD record
ord-f2b2c16d9a1e43edbc7938478bdf5ea5
Source dataset
uspto-grants-2010_10
Patent number
US07814713B2

Reaction notes

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