Methanol → Cyclohexylfulvene

HRID 1251529Notes

Reaction equation

HRID 1251529 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]1(=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CO.N1CCC[CH2:16]1>O.C(O)(=O)C>[CH:6]1([C:2]2[C:1](=[CH2:16])[CH:5]=[CH:4][CH:3]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 887MethanolHCID 7612CyclopentadieneHCID 7967CyclohexanoneHCID 31268Pyrrolidine

Product 1

HCID 22327799CyclohexylfulveneYield 92.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

8.2 ml (100 mmol) of cyclopentadiene and 4.2 ml (40 mmol) of cyclohexanone were added to 40 ml of dehydrated methanol, and 5.0 ml (60 mmol) of pyrrolidine were then added dropwise at 0° C. Then, reaction was carried out at room temperature for 3 hours. Next, 3.8 ml of acetic acid were slowly added at 0° C., and 20 ml of water were further added, followed by extraction with diethyl ether. The resultant organic phase, after washed with water, was dried over magnesium sulfate, and the used solvent was then distilled off to obtain 5.95 g of a yellow liquid.

Workup

  1. additionwere then added dropwise at 0° C
  2. customThen, reaction
  3. extractionfollowed by extraction with diethyl ether
  4. washThe resultant organic phase, after washed with water
  5. dry with materialwas dried over magnesium sulfate
  6. distillationthe used solvent was then distilled off

Sources & evidence

ORD record
ord-ac64bae7b4274fdc8052ee9019980cbe
Source dataset
uspto-grants-2002_01
Patent number
US06342568B1

Reaction notes

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