Hydroquinone → HCID 12491640, compound

HRID 970944Notes

Reaction equation

HRID 970944 reaction equation
C1[CH:5]2[C@@H:6]3[CH:10]=[CH:9][C@H:8]([CH:4]2C=C1)[CH2:7]3.[CH3:11][O:12][C:13](=[O:16])C=C.C1(C=CC(O)=CC=1)O>>[CH3:11][O:12][C:13]([C:6]12[CH2:7][CH:8]([CH2:4][CH2:5]1)[CH:9]=[CH:10]2)=[O:16]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 7294Methyl AcrylateHCID 15618652endo-Dicyclopentadiene

Product 1

HCID 12491640HCID 12491640, compoundYield 86%

Conditions

Temperature
180 °C

Procedure

DCPD (dicyclopentadiene, Aldrich, 256.5 mL, 1.9 mol), methylacrylate (Aldrich, 405 mL, 4.5 mol), and hydroquinone (3.2 g, 0.03 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 at 1 torr using a vacuum pump at 50° C. to obtain the product (yield: 86%). The mole ratio (mol %) of exo-isomers to endo-isomers of the product was 41.1:58.9.

Workup

  1. customreaction
  2. temperaturethe reaction mixture was cooled down
  3. distillationThe reaction mixture was distilled at 1 torr
  4. customat 50° C.

Sources & evidence

ORD record
ord-76880ffd5ee9485dad1a70cd637e534e
Source dataset
uspto-grants-2007_12
Patent number
US07312285B2

Reaction notes

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