Hydroquinone → 5-Norbornene 2-allylacetate

HRID 507732Notes

Reaction equation

HRID 507732 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 (dicyclopentadiene, Aldrich, 248 ml, 1.852 mol), allylacetate (Aldrich, 500 ml, 4.63 mol) and hydroquinone (0.7 g, 0.006 mol) were charged into a 2 L high-pressure autoclave, and the temperature was raised to 190° C. The resulting mixture was reacted for 5 hours with stirring at 300 rpm. After the reaction was completed, the reaction mixture was cooled and transferred to a distilling apparatus. The reaction mixture was distilled twice under a reduced pressure (1 torr) using a vacuum pump to yield the title compound at 56° C. (yield: 30%, exo/endo=57/43).

Workup

  1. customThe resulting mixture was reacted for 5 hours
  2. temperaturethe reaction mixture was cooled
  3. distillationThe reaction mixture was distilled twice under a reduced pressure (1 torr)

Sources & evidence

ORD record
ord-aabd324df85248e087b606339e669a74
Source dataset
uspto-grants-2010_08
Patent number
US07786230B2

Reaction notes

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