Benzene → 2-Methylene-5,8-dioxaspiro[3.4]octane

HRID 1966816Notes

Reaction equation

HRID 1966816 reaction equation
Br[CH2:2][CH:3]1[CH2:6][C:5]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:4]1.[OH-].[Na+].C1C=CC=CC=1>O>[CH2:2]=[C:3]1[CH2:6][C:5]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:4]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 667332822-(Bromomethyl)-5,8-dioxaspiro[3.4]octane

Product 1

HCID 667332232-Methylene-5,8-dioxaspiro[3.4]octane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(bromomethyl)-5,8-dioxaspiro[3.4]octane (1.3 gm, 6.28 mmol) (step e), polyethylene glycol (PEG-600) (0.5 gm), 50% aqueous sodium hydroxide solution (5 ml) and benzene was refluxed for about 12 hours. The reaction mixture was cooled, diluted with water and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure to get a crude product, which was purified by column chromatography.

Workup

  1. temperaturewas refluxed for about 12 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce7d606590aa4187ac24494bc354bece
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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