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

HRID 1195300
Notes
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Reaction equation

HRID 1195300 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 8028Tetrahydrofuran
Solvent

Conditions

Temperature
-40 °C

Procedure

32 ml of a 1.4 M solution of methyllithium in diethyl ether was dissolved in 50 ml of anhydrous tetrahydrofuran. The obtained solution was cooled to -40° C. in a nitrogen atmosphere, followed by the addition of 5.0 g of solid (6-methyl-1,3-benzodioxol-5-yl)carboxaldehyde. The mixture was heated to a room temperature over a period of one hour, followed by the addition of water. The obtained mixture was extracted with ether and the obtained organic layer was washed with an aqueous solution of common salt, dried over magnesium sulfate and distilled to remove the solvent. The obtained white solid was recrystallized from diisopropyl ether/n-hexane to obtain 2.8 g of the title compound as a colorless crystal.

Workup

  1. temperatureThe mixture was heated to a room temperature over a period of one hour
  2. extractionThe obtained mixture was extracted with ether
  3. washthe obtained organic layer was washed with an aqueous solution of common salt
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe obtained white solid was recrystallized from diisopropyl ether/n-hexane

Sources & evidence

ORD record
ord-0e904d4f277f4e3b923ad74d8b62d5b6
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05110956

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes