Sodium Sulfate → 2-Propen-1-ol, 2-methyl-3-(4-methylphenyl)-, (2E)-

HRID 1957917Notes

Reaction equation

HRID 1957917 reaction equation
[CH3:1]/[C:2](=[CH:5]\[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)/[CH:3]=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1]/[C:2](=[CH:5]\[C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1)/[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 11984401HCID 11984401, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 156834112-Propen-1-ol, 2-methyl-3-(4-methylphenyl)-, (2E)-Yield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2E)-2-methyl-3-(4-methylphenyl)-2-propenal (320 g, 2 mol, described in Tet. Let., 28, 1987, 1263) was dissolved under nitrogen in dry THF (1 liter). The solution was cooled in an ice-water bath and solid lithium aluminum hydride (25 g, 0.63 mol) was added portion-wise at a rate such as to maintain the internal temperature below 20° C. The cooling bath was removed and the reaction stirred for 3 hours. It was then recooled in an ice-water bath. Water (25 ml) was added slowly to the reaction, followed by 5% aqueous NaOH (75 ml) and more water (25 ml). The cooling bath was removed and the reaction stirred until a white slurry was obtained (30 minutes). Solid anhydrous sodium sulfate (100 g) was added to the reaction. After stirring for an additional 15 minutes, the solid was filtered off and thoroughly rinsed with diethyl ether. The filtrate was then concentrated under vacuum. The product was purified by distillation through a 20-cm Widmer column. 304 g of the desired alcohol were obtained (1.78 mol, 89% yield).

Workup

  1. temperatureThe solution was cooled in an ice-water bath
  2. temperatureto maintain the internal temperature below 20° C
  3. customThe cooling bath was removed
  4. customIt was then recooled in an ice-water bath
  5. additionWater (25 ml) was added slowly to the reaction
  6. customThe cooling bath was removed
  7. stirringthe reaction stirred until a white slurry
  8. customwas obtained (30 minutes)
  9. stirringAfter stirring for an additional 15 minutes
  10. filtrationthe solid was filtered off
  11. washthoroughly rinsed with diethyl ether
  12. concentrationThe filtrate was then concentrated under vacuum
  13. distillationThe product was purified by distillation through a 20-cm Widmer column

Sources & evidence

ORD record
ord-62e3e4478a964cf08a6c1912b2a937e5
Source dataset
uspto-grants-2013_04
Patent number
US08410042B2

Reaction notes

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