Hydroquinone → Allylacetate Norbornene

HRID 2117778Notes

Reaction equation

HRID 2117778 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
190 °C

Procedure

DCPD (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 190° C., reaction was carried out for 5 hours while stirring the autoclave 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 at 1 torr twice using a vacuum pump at 56° C. to obtain the product (yield: 30%). The molar ratio (mol %) of exo/endo isomers of the product was 57:43.

Workup

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

Sources & evidence

ORD record
ord-c52287183153422ab6fbeb6c1fbf1307
Source dataset
uspto-grants-2008_10
Patent number
US07442752B2

Reaction notes

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