Hydroquinone → Allylacetate Norbornene

HRID 970946Notes

Reaction equation

HRID 970946 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]([CH2:9][CH2:10]1)[CH:4]=[CH:5]2.[CH2:11]([CH2:14][C:15]([OH:17])=[O:16])[CH:12]=[CH2:13]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 50778374-PentenoateHCID 15618652endo-Dicyclopentadiene

Product 1

HCID 67194674Allylacetate NorborneneYield 30%

Conditions

Temperature
180 °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 put in a 2 L autoclave. After heating to 180° C., reaction was carried out for 5 hours while stirring at 300 rpm. After the reaction was completed, the reaction mixture was cooled down and transferred to a distillation unit. The reaction mixture was distilled twice at 1 torr using a vacuum pump at 56° C. to obtain the product (yield: 30%). The mole ratio (mol %) of the exo-isomers to endo-isomers of the product was 17:83.

Workup

  1. customreaction
  2. temperaturethe reaction mixture was cooled down
  3. distillationThe reaction mixture was distilled twice at 1 torr
  4. customat 56° C.

Sources & evidence

ORD record
ord-58cadddb38334df089dec7c44fa541ca
Source dataset
uspto-grants-2007_12
Patent number
US07312285B2

Reaction notes

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