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

HRID 858205Notes

Reaction equation

HRID 858205 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 1 M solution of lithium aluminum hydride in tetrahydrofuran are added with ice-cooling. After 30 minutes of stirring at room temperature, a saturated ammonium chloride solution is added and the pH is adjusted to neutral by addition of a 5% strength citric acid solution. 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 magnesium sulfate and the solvent is then removed under reduced pressure. This gives 10.5 g of cis-3-hydroxymethylcyclohexanol as a colorless oil. C7H14O2 (130.13), Rf(ethyl acetate)=0.14.

Workup

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

Sources & evidence

ORD record
ord-679154e595174144b48cd57870b06498
Source dataset
uspto-grants-2006_12
Patent number
US07148246B2

Reaction notes

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