Dimedone → 51335-83-2

HRID 1421649Notes

Reaction equation

HRID 1421649 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[CH2:3]1.[BH4-].[Na+].CO.O>C1COCC1>[CH3:1][C:2]1([CH3:10])[CH2:3][CH:4]([OH:5])[CH2:6][CH:7]([OH:8])[CH2:9]1

Participants

5

Reactant 3

HCID 31358DimedoneHCID 4311764Sodium borohydrideHCID 22242641Methanol--water (1/1)

Product 1

HCID 26510851335-83-2

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

14.0 g (0.1 mol) of dimedone were dissolved in 200 ml of THF. 3.8 g (0.1 mol) of NaBH4 and 5 mmol of CeCl3 dissolved in 50 ml of THF were then added at -30° C. The mixture was stirred at room temperature for another 2 hours and was hydrolyzed at 0° C. by means of methanol/water. The organic phase was separated off and the solvent was removed. The residue was extracted with ethanol and unreacted dimedone was removed by crystallization. This gave 11.5 g (80%) of 5,5-dimethylcyclohexane-1,3-diol.

Workup

  1. additionwere then added at -30° C
  2. customThe organic phase was separated off
  3. customthe solvent was removed
  4. extractionThe residue was extracted with ethanol and unreacted dimedone
  5. customwas removed by crystallization

Sources & evidence

ORD record
ord-af0ea399c8674ba7b628a1320df87b8f
Source dataset
uspto-grants-2000_06
Patent number
US06077965

Reaction notes

Loading…