Ethylene Glycol → HCID 68865936, compound

HRID 1454766Notes

Reaction equation

HRID 1454766 reaction equation
[C:1]([C:4]12[CH2:13][CH:8]([C:9]([CH3:12])=[CH:10][CH2:11]1)[C:7](=[O:14])[CH2:6][CH:5]2[CH3:15])([CH3:3])=[CH2:2].[CH2:16](O)[CH2:17][OH:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1CCCCC1>[CH3:15][CH:5]1[C:4]2([C:1]([CH3:3])=[CH2:2])[CH2:13][CH:8]([CH:9]([CH3:12])[CH2:10][CH2:11]2)[C:7]2([O:18][CH2:17][CH2:16][O:14]2)[CH2:6]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 68526884HCID 68526884, compound

Product 1

HCID 68865936HCID 68865936, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A soln. of 2.0 g of 5-isopropenyl-4,8-dimethylbicyclo[3.3.1]non-7-en-2-one (9.8 mmol) in 100 ml cyclohexane was treated with 1.8 g ethyleneglycol (2.9 mmol, 3.0 eq.) and 0.2 g para-toluenesulfonic acid mono hydrate (1.0 mmol 0.1 eq.). The soln. obtained was heated at reflux for 3 h (Dean-Stark apparatus), cooled and poured into aq. sat. NaHCO3 soln. (100 ml). Extraction with MTBE (2×80 ml) followed by washing of the aq. phases with H2O (100 ml) and aq. sat. NaCl soln. (150 ml), drying of org. phases over MgSO4 led to 2.6 g of crude product. FC (SiO2, hexane/MTBE 19:1) gave 0.76 g (31%) of compound 6 as colorless liquid. The boiling point of the end product is 130° C. at 0.09 mbar. Rf (hexane/MTBE 19:1) 0.47.

Workup

  1. customobtained
  2. temperaturewas heated
  3. temperatureat reflux for 3 h (Dean-Stark apparatus)
  4. temperaturecooled
  5. extractionExtraction with MTBE (2×80 ml)
  6. washby washing of the aq. phases with H2O (100 ml) and aq. sat. NaCl soln
  7. custom(150 ml), drying of org

Sources & evidence

ORD record
ord-1b78ff1bd1a94b3ab2e050fa091fb9e3
Source dataset
uspto-grants-2009_01
Patent number
US07482313B2

Reaction notes

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