Allyl Alcohol → Bicyclo(2.2.1)hept-5-ene-2-methanol

HRID 1982745Notes

Reaction equation

HRID 1982745 reaction equation
C1[CH:5]2[C@@H:6]3[CH:10]=[CH:9][C@H: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 7858Allyl AlcoholHCID 15618652endo-Dicyclopentadiene

Product 1

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

Conditions

Temperature
210 °C

Procedure

After DCPD (dicyclopentadiene, Aldrich, 397 g, 3 mol) and allyl alcohol (Aldrich, 331 g, and 5.7 mol) were put into a 2 L high pressure reactor, temperature was increased to 210° C. After a reaction was conducted for 1 hour while agitating at 300 rpm, reactants were cooled and moved to a distillator. Distillation was repeatedly conducted under reduced pressure of 1 torr using a vacuum pump twice to obtain a product at 56° C. (yield: 52%)

Workup

  1. temperaturewere cooled
  2. distillationDistillation
  3. customto obtain a product at 56° C. (yield: 52%)

Sources & evidence

ORD record
ord-10ff122a93ee4c65a4ec76d5db7516ed
Source dataset
uspto-grants-2009_06
Patent number
US07541073B2

Reaction notes

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