Hydroquinone → HCID 12491640, compound

HRID 2117770Notes

Reaction equation

HRID 2117770 reaction equation
C1[CH:5]2[C@@H:6]3[CH:10]=[CH:9][C@H:8]([CH:4]2C=C1)[CH2:7]3.[C:11]([O:15][CH3:16])(=[O:14])C=C.C1(C=CC(O)=CC=1)O>>[CH3:16][O:15][C:11]([C:6]12[CH2:7][CH:8]([CH2:4][CH2:5]1)[CH:9]=[CH:10]2)=[O:14]

Participants

4

Reactant 3

HCID 785HydroquinoneHCID 7294Methyl AcrylateHCID 15618652endo-Dicyclopentadiene

Product 1

HCID 12491640HCID 12491640, compoundYield 88.1%

Conditions

Temperature
200 °C

Procedure

DCPD (Aldrich, 256.5 mL, 1.9 mol), methyl acrylate (Aldrich, 405 mL, 4.5 mol), and hydroquinone (3.2 g, 0.03 mol) were put in a 2 L autoclave. After heating to 200° 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 using a vacuum pump at 50° C. to obtain the product (yield: 88.1%). The molar ratio (mol %) of exo/endo isomers of the product was 54.5:45.5.

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-47817d6779de4b31b74e0ca8466d5231
Source dataset
uspto-grants-2008_10
Patent number
US07442752B2

Reaction notes

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