Ethylene Glycol → 1,4-Dioxaspiro[4.5]decan-8-ylmethanol

HRID 2043905Notes

Reaction equation

HRID 2043905 reaction equation
[C:1](CC1CCC(=O)CC1)(O)=[O:2].[CH2:12]([OH:15])[CH2:13][OH:14].[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[O:14]1[C:16]2([CH2:21][CH2:20][CH:19]([CH2:1][OH:2])[CH2:18][CH2:17]2)[O:15][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 241BenzeneHCID 99204382-(4-oxocyclohexyl)acetic Acid

Product 1

HCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-carboxymethylcyclohexanone (21 g), ethylene glycol (19 g) and benzene (250 mL) was heated at reflux for 20 h with Dean Stark azeotropic removal of water. After cooling the solution was washed with sodium bicarbonate solution, dried over magnesium sulphate and concentrated. The crude ketal was then taken up in diethyl ether (250 mL) and lithium aluminium hydride (7 g) was added. The mixture was stirred overnight and then water (20 mL), 10% sodium hydroxide (30 mL) and water (30 mL) was added carefully. Sodium sulphate (30 g) was then added and the mixture stirred for 20 min, The insoluble material was removed by filtration and the organic phase concentrated in vacuo to give (1,4-dioxaspiro[4.5]dec-8-yl)-methanol (21 g).

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling the solution
  3. washwas washed with sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. additionlithium aluminium hydride (7 g) was added
  7. additionwater (20 mL), 10% sodium hydroxide (30 mL) and water (30 mL) was added carefully
  8. additionSodium sulphate (30 g) was then added
  9. stirringthe mixture stirred for 20 min
  10. customThe insoluble material was removed by filtration
  11. concentrationthe organic phase concentrated in vacuo

Sources & evidence

ORD record
ord-f331cb58e47f4e19b08e1b8dc310f43a
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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