Citric Acid → rel-(1R,3S)-3-Hydroxycyclohexanemethanol

HRID 553574Notes

Reaction equation

HRID 553574 reaction equation
[CH:1]12[CH2:9][CH:5]([O:6][C:7]1=[O:8])[CH2:4][CH2:3][CH2:2]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[OH:8][CH2:7][C@@H:1]1[CH2:2][CH2:3][CH2:4][C@H:5]([OH:6])[CH2:9]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 25517Ammonium ChlorideHCID 2969126-Oxabicyclo(3.2.1)octan-7-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 15727328rel-(1R,3S)-3-Hydroxycyclohexanemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10 g of 6-oxabicyclo[3.2.1]octan-7-one are dissolved in 300 ml of tetrahydrofuran, and 160 ml of a 1M solution of lithium aluminum hydride in tetrahydrofuran are added with ice cooling. After 30 minutes of stirring at room temperature, saturated ammonium chloride solution is added and the pH is adjusted to neutral by addition of a 5% strength solution of citric acid. The tetrahydrofuran is removed under reduced pressure and the residue is extracted three times with in each case 150 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and the solvent is then removed under reduced pressure. This gives 10.5 g of (1S,3R)/(1R,3S)-3-hydroxymethylcyclohexanol as a colorless oil. C7H14O2 (130.13), Rf(ethyl acetate)=0.14.

Workup

  1. customThe tetrahydrofuran is removed under reduced pressure
  2. extractionthe residue is extracted three times with in each case 150 ml of ethyl acetate
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. customthe solvent is then removed under reduced pressure

Sources & evidence

ORD record
ord-691b8c24165442aa9eff3647f248199a
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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