Ethylene Glycol → HCID 66936799, compound

HRID 1364002Notes

Reaction equation

HRID 1364002 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:12].[OH:13][CH2:14][CH2:15]O>C1(C)C=CC=CC=1>[O:12]1[C:2]2([CH2:3][CH2:4][CH2:5][C:6]3([CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]3)[CH2:1]2)[O:13][CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 24974018HCID 24974018, compound

Product 1

HCID 66936799HCID 66936799, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the relevant spiro[5.5]undec-7-en-2-one isomer (10) or (10′) (10 g, 61 mmol) in toluene (150 mL) was added HO(CH2)2OH (10 mL, 179 mmol) and p-toluenesulfonic acid H2O (0.57 g, 3 mmol). The reaction mixture was brought to reflux and the H2O generated was removed by azeotropic distillation (using a Dean-Stark separator). The reaction mixture was then cooled and washed with a saturated NaHCO3 solution. The aqueous phase was extracted with Et2O and the combined organic layers dried over anhydrous Na2SO4. The solvent was removed in vacuo and the resulting residue purified over silica (isooctane/EtOAc, 95:5) to afford 12.1 g (95% yield) of the desired product which was characterized as follows:

Workup

  1. temperatureto reflux
  2. customthe H2O generated was removed by azeotropic distillation (
  3. temperatureThe reaction mixture was then cooled
  4. washwashed with a saturated NaHCO3 solution
  5. extractionThe aqueous phase was extracted with Et2O
  6. dry with materialthe combined organic layers dried over anhydrous Na2SO4
  7. customThe solvent was removed in vacuo
  8. customthe resulting residue purified over silica (isooctane/EtOAc, 95:5)

Sources & evidence

ORD record
ord-3457f0a003374199955be40aed3e4c1c
Source dataset
uspto-grants-2011_02
Patent number
US07888338B2

Reaction notes

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