Tetrahydrofuran → 2-Hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylate

HRID 1276022Notes

Reaction equation

HRID 1276022 reaction equation
[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[C:7]([O:11][CH2:12][CH2:13][OH:14])(=[O:10])C=C.[CH2:15]1COC[CH2:16]1>>[CH:2]12[CH2:16][CH2:15][CH:5]([CH:6]=[CH:1]1)[CH2:4][CH:3]2[C:7]([O:11][CH2:12][CH2:13][OH:14])=[O:10]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 116051,3-CyclohexadieneHCID 131652-Hydroxyethyl acrylate

Product 1

HCID 184136662-Hydroxyethyl bicyclo[2,2,2]oct-5-ene-2-carboxylateYield 51%

Procedure

Cyclohexadiene (80 g) and 140 g of 2-hydroxyethyl acrylate were dissolved in 500 g of THF solvent. After reacting at 50° C. for 24 hours, the solvent was removed by rotary evaporator. The residue was distilled under reduced pressure to obtain 100 g of 2-hydroxyethyl bicyclo[2,2,2]oct-5-ene-2- carboxylate as a mixture of endo and exo (yield: 45%).

Workup

  1. customthe solvent was removed by rotary evaporator
  2. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-fc14b68eaa4a4e5d9c807ccda287c9ba
Source dataset
uspto-grants-2000_12
Patent number
US06165672

Reaction notes

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