Acetone → 2-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

HRID 1787399Notes

Reaction equation

HRID 1787399 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][CH:12]1[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:14][CH2:13]1)C.CC(C)=O.[OH-].[Na+]>C1COCC1>[O:16]1[C:15]2([CH2:20][CH2:21][CH:12]([CH2:11][CH2:10][OH:9])[CH2:13][CH2:14]2)[O:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 15700391Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 118054582-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-olYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
3 °C

Procedure

Third Step: 20.0 g of lithium aluminum hydride (LAH) and 800 mL of THF were added to a reactor under nitrogen atmosphere, and stirred at 3° C. 190.0 g of the compound (12) dissolved in 200 mL of THF was added dropwise thereto at a temperature range of from 0 to 7° C. over 2 hours, followed by further stirring at 0° C. for 3 hours. After confirming that the reaction had been completed by GC analysis, a mixture of 60 mL of THF and 60 mL of acetone was added dropwise thereto at 0° C. over 30 minutes, and 100 mL of a 2N sodium hydroxide aqueous solution was further added dropwise thereto at 10° C. over 30 minutes. A white solid thus deposited was filtered off, and 300 mL of toluene and 1,000 mL of brine were added to and mixed with the filtrate. The mixture was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with brine, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure to obtain 152.7 g of 2-(1,4-dioxaspiro[4,5]dec-8-yl)ethanol (13) as a colorless liquid.

Workup

  1. additionwas added dropwise
  2. stirringby further stirring at 0° C. for 3 hours
  3. additionwas added dropwise
  4. waitat 0° C. over 30 minutes
  5. waitat 10° C. over 30 minutes
  6. filtrationA white solid thus deposited was filtered off
  7. addition300 mL of toluene and 1,000 mL of brine were added to and
  8. additionmixed with the filtrate
  9. customThe mixture was separated into an organic layer
  10. extractionextraction to the organic layer
  11. washwashed with brine
  12. dry with materialby drying over anhydrous magnesium sulfate
  13. customThereafter, the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-5fadece5a1ce4652ac2d89ceccc5b5c3
Source dataset
uspto-grants-2009_03
Patent number
US07510749B2

Reaction notes

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