Dicyclopentadiene → Bicyclo(2.2.1)hept-5-ene-2-methanol

HRID 1713959Notes

Reaction equation

HRID 1713959 reaction equation
C1[CH:5]2[CH:6]3[CH:10]=[CH:9][CH:8]([CH:4]2[CH:3]=C1)[CH2:7]3.C([OH:14])C=C>>[CH:8]12[CH2:7][CH:6]([CH:10]=[CH:9]1)[CH2:5][CH:4]2[CH2:3][OH:14]

Participants

3

Reactant 2

HCID 6492DicyclopentadieneHCID 7858Allyl Alcohol

Product 1

HCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanolYield 52%

Conditions

Temperature
210 °C

Procedure

397 g (3 mol) of dicyclopentadiene (DCPD) (produced from Aldrich Inc.) and 331 g (5.7 mol) of allyl alcohol (produced from Aldrich Inc.) were added to a 2 L high-pressure reactor and the temperature of the 2 L high-pressure reactor was increased to 210° C. The resulting mixture was reacted for one hour, stirring at 300 rpm. When the reaction was completed, the reactant was cooled and loaded into a distillation device. The reactant was distilled twice at a reduced pressure of 1 torr using a vacuum pump to attain a product at 56° C. (Yield: 52%).

Workup

  1. customThe resulting mixture was reacted for one hour
  2. temperaturethe reactant was cooled
  3. distillationThe reactant was distilled twice at a reduced pressure of 1 torr
  4. customat 56° C.

Sources & evidence

ORD record
ord-7d958a33a40445429a0bb3af7b35594c
Source dataset
uspto-grants-2010_09
Patent number
US07795361B2

Reaction notes

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