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

HRID 1956746Notes

Reaction equation

HRID 1956746 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 filtraion. 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. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b93e5a952a24e729193f7b1682997e4
Source dataset
uspto-grants-1998_07
Patent number
US05780632

Reaction notes

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