Ethylene Glycol → HCID 85846260, compound

HRID 2249889Notes

Reaction equation

HRID 2249889 reaction equation
[CH2:1]=[C:2]1[CH2:8][CH:7]2[C:9](=[O:10])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.[CH2:11](O)[CH2:12][OH:13].CCN(CC)CC.[O-]S([O-])(=O)=O.[Mg+2]>C1C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:12]1[O:13][C:9]2([CH:7]3[CH2:6][CH2:5][CH:4]2[CH2:3][C:2](=[CH2:1])[CH2:8]3)[O:10][CH2:11]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 14174917HCID 14174917, compound

Product 1

HCID 85846260HCID 85846260, compoundYield 112%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 3-methylene bicyclo[3,2,1]octan-8-one (0.14 g, 1.04 mmol, 1.0 eq.) in benzene (10 mL) was added ethylene glycol (0.65 g, 16 eq.) and PTSA (0.01 g, 0.06 eq.). The reaction was equipped with a Dean-Stark and heated at reflux overnight. After cooling to room temperature, Et3N (0.15 mL) was introduced and the resulting mixture was passed through a cake of SiO2 and MgSO4. The cake was washed with CH2Cl2 and the combined filtrates were concentrated to give 3-methylene bicyclo[3,2,1]octan-8-one ethylene ketal (0.21 g, >100%).

Workup

  1. customThe reaction was equipped with a Dean-Stark
  2. temperatureheated
  3. temperatureat reflux overnight
  4. washThe cake was washed with CH2Cl2
  5. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-63e569fe0b6b43e5959bb33c0466ed79
Source dataset
uspto-grants-2008_01
Patent number
US07314936B2

Reaction notes

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