Sodium Hydroxide → Cyclohexane-1,1-diethanol

HRID 2223853Notes

Reaction equation

HRID 2223853 reaction equation
[C:1]1([CH2:11][C:12](O)=[O:13])([CH2:7][C:8](O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O.C(OCC)C>[OH:9][CH2:8][CH2:7][C:1]1([CH2:11][CH2:12][OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 78061Cyclohexanediacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 76657Cyclohexane-1,1-diethanolYield 93.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1,-cyclohexanediacetic acid (6.0 g) in tetrahydrofuran (90 mL) was added lithium aluminum hydride (2.28 g) under ice cooling. The solution was stirred under reflux for 4 hours, and then, cooled on ice, to which diethyl ether (200 mL), water (2.3 mL) and a 15% aqueous sodium hydroxide solution (2.3 mL) were added. After stirring the solution at room temperature for 30 minutes, water (6.9 mL) was added and the solution was stirred at room temperature for additional 30 minutes. Anhydrous magnesium sulfate was added to the solution, and it was filtered under reduced pressure. The filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, ethyl acetate) to give the title compound (4.83 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. stirringAfter stirring the solution at room temperature for 30 minutes
  3. stirringthe solution was stirred at room temperature for additional 30 minutes
  4. filtrationwas filtered under reduced pressure
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-798aaa5bc07c45c9927fa92bfb264012
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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