Water → rel-(1R,2R)-1,2-Cyclohexanedimethanol

HRID 1956744Notes

Reaction equation

HRID 1956744 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@@H:7]12[C:16](=O)[O:15][C:13](=[O:14])[C@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12]2.O>C(OCC)C>[OH:14][CH2:13][C@@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]1[CH2:16][OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 12261141(-)-trans-1,2-Cyclohexanedicarboxylic AnhydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11217323rel-(1R,2R)-1,2-CyclohexanedimethanolYield 70.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a mixture of lithium aluminum hydride (2.85 g; 75 mmol) and diethyl ether (50 ml), a solution of trans-1,2-cyclohexanedicarboxylic acid anhydride (1) (7.71 g; 50 mmol) in diethyl ether (150 ml) is dropwise added, and the resultant mixture is allowed to react at room temperature for 3 hours and then heated under reflux for 2 hours. After cooling, wet ether is dropwise added to the reaction mixture, followed by addition of water. The organic layer is collected by decantation, followed by concentration to give trans-1,2-bis(hydroxymethyl)cyclohexane (2) (5.1 g).

Workup

  1. customto react at room temperature for 3 hours
  2. temperatureheated
  3. temperatureunder reflux for 2 hours
  4. temperatureAfter cooling
  5. customThe organic layer is collected by decantation
  6. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-2734146dc1ba4d45a5ef5ffea48237df
Source dataset
uspto-grants-1998_07
Patent number
US05780632

Reaction notes

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