Ethyl Bromide → 1-(6-Methylbenzo[d][1,3]dioxol-5-yl)propan-1-ol

HRID 2259773Notes

Reaction equation

HRID 2259773 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]2[O:10][CH2:11][O:12][C:4]=2[CH:3]=1.[Mg].Br[CH2:15][CH3:16].[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:15][CH3:16])=[CH:6][C:5]2[O:10][CH2:11][O:12][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 31462426-Methyl-2H-1,3-benzodioxole-5-carbaldehydeHCID 5462224Magnesium

Product 1

HCID 145148971-(6-Methylbenzo[d][1,3]dioxol-5-yl)propan-1-olYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.0 g of (6-methyl-1,3-benzodioxol-5-yl)-carboxaldehyde in 15 ml of anhydrous tetrahydrofuran was dropwise added at a room temperature to a Grignard reagent prepared from 0.32 g of magnesium ribbon, 20 ml of anhydrous tetrahydrofuran and 1.4 g of bromoethane, followed by stirring for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture and the obtained mixture was distilled to remove the solvent. The residue was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.27 g of the title compound as a colorless crystal.

Workup

  1. distillationthe obtained mixture was distilled
  2. customto remove the solvent
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in a vacuum
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2:8)

Sources & evidence

ORD record
ord-894943c2c9fb4699b9e0464ebbdbf4d4
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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