Water → 1-(6-Methyl-1,3-benzodioxol-5-yl)ethanol

HRID 486890Notes

Reaction equation

HRID 486890 reaction equation
[CH3:1][Li].[CH3:3][C:4]1[C:9]([CH:10]=[O:11])=[CH:8][C:7]2[O:12][CH2:13][O:14][C:6]=2[CH:5]=1.O>C(OCC)C.O1CCCC1>[CH3:3][C:4]1[C:9]([CH:10]([OH:11])[CH3:1])=[CH:8][C:7]2[O:12][CH2:13][O:14][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 31462426-Methyl-2H-1,3-benzodioxole-5-carbaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 145148961-(6-Methyl-1,3-benzodioxol-5-yl)ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

32 ml of a 1.4M solution of methyllithium in diethyl ether was dissolved in 50 ml of anhydrous tetrahydrofuran and the solution was cooled at -40° C. in a nitrogen atmosphere. 5.0 g of solid (6-methyl-1,3-benzodioxol-5-yl) carboxaldehyde was added to the solution and the temperature was elevated to room temperature gradually over 1 h. Water was added to the reaction mixture. After extraction with ether, the organic layer was washed with an aqueous common salt solution. After drying over magnesium sulfate, the solvent was distilled off to obtain a white solid, which was recrystallized from diisopropyl ether/n-hexane to obtain 2.8 g of the intended compound in the form of white crystals.

Workup

  1. extractionAfter extraction with ether
  2. washthe organic layer was washed with an aqueous common salt solution
  3. dry with materialAfter drying over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customto obtain a white solid, which
  6. customwas recrystallized from diisopropyl ether/n-hexane

Sources & evidence

ORD record
ord-1ec77b5659234381a93e3e48556e8f1c
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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