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

HRID 1517149Notes

Reaction equation

HRID 1517149 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 67%

Conditions

Temperature
190 °C

Procedure

132 g (1 mol) of dicyclopentadiene and 116.2 g (2 mol) of allyl alcohol were placed into a 300 ml high-pressure reactor and stirred at 190° C. for 3 to 4 hours. The resulting solution was distilled at 80° C. under vacuum to give 5-norbornene-2-methanol. (Yield: 67%, 166 g)

Workup

  1. distillationThe resulting solution was distilled at 80° C. under vacuum

Sources & evidence

ORD record
ord-6f99db75e4104996ae17d31b138b7e7b
Source dataset
uspto-grants-2012_07
Patent number
US08231946B2

Reaction notes

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