Diethyl Ether → rel-(1R,2R)-1,2-Cyclohexanedimethanol

HRID 1734227Notes

Reaction equation

HRID 1734227 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@@H:7]1([C:16](O)=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[C:13](O)=[O:14].CCOCC>O1CCCC1>[OH:14][CH2:13][C@@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]1[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 720895(1R,2R)-(-)-1,2-Cyclohexanedicarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11217323rel-(1R,2R)-1,2-CyclohexanedimethanolYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of lithium aluminum hydride (52.22 g; 1,374 mol) and tetrahydrofuran (500 ml), a solution of trans-1,2-cyclohexanedicarboxylic acid (5) (118.18 g; 0.687 mol) in tetrahydrofuran (2 liters) is dropwise added under reflux, and the resultant mixture is allowed to react under reflux for 3 hours. After completion of the reaction, the reaction mixture is cooled, and wet tetrahydrofuran and ether are dropwise added thereto, followed by filtration. The filtrate is concentrated under reduced pressure to give trans-1,2-bis(hydroxymethyl)cyclohexane (2) (71.86 g).

Workup

  1. temperatureunder reflux
  2. customto react
  3. temperatureunder reflux for 3 hours
  4. customAfter completion of the reaction
  5. temperaturethe reaction mixture is cooled
  6. filtrationfollowed by filtration
  7. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2ac88a0678f4cb88f1896f237e93ccd
Source dataset
uspto-grants-1996_07
Patent number
US05532372

Reaction notes

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