Sodium Hydroxide → HCID 24885944, compound

HRID 1821143Notes

Reaction equation

HRID 1821143 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH2:22][O:23]C(=O)CC)[O:9][CH2:8][C:7]2([CH2:14][O:13][C:12]([CH3:21])([CH2:15][O:16]C(=O)CC)[O:11][CH2:10]2)[CH2:6][O:5]1>O.CO>[CH3:21][C:12]1([CH2:15][OH:16])[O:11][CH2:10][C:7]2([CH2:6][O:5][C:4]([CH3:3])([CH2:22][OH:23])[O:9][CH2:8]2)[CH2:14][O:13]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 24885943HCID 24885943, compound

Product 1

HCID 24885944HCID 24885944, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of sodium hydroxide (3 g, 0.075 mol) in water (25 ml) and methanol (25 ml), 3,9-dimethyl-3,9-bis(propionyloxymethyl)-2,4,8,10-tetraoxaspiro[5,5]undecane (6.5 g, 18 mmol) was slowly added, followed by stirring for 40 minutes at 60° C. After the solvent was distilled off under reduced pressure, the resultant concentrate residue was dissolved in acetonitrile/brine. The separated-off organic layer was concentrated under reduced pressure, and then ethyl acetate was added thereto. After the insoluble material was filtered out, the resultant filtrate was concentrated again under reduced pressure. The resultant concentrate residue was recrystallized from ethyl acetate/hexane, to give 3,9-dimethyl-3,9-bis(hydroxymethyl)-2,4,8,10-tetraoxaspiro[5,5]undecane (3.4 g, 13.7 mmol, yield 76%).

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. concentrationthe resultant concentrate residue
  3. dissolutionwas dissolved in acetonitrile/brine
  4. concentrationThe separated-off organic layer was concentrated under reduced pressure
  5. additionethyl acetate was added
  6. filtrationAfter the insoluble material was filtered out
  7. concentrationthe resultant filtrate was concentrated again under reduced pressure
  8. concentrationThe resultant concentrate residue
  9. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8d3f56f120934ae8b79393c67305407e
Source dataset
uspto-grants-2009_10
Patent number
US07605276B2

Reaction notes

Loading…