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

HRID 486891Notes

Reaction equation

HRID 486891 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 added dropwise at 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. The mixture was stirred for 2 h. A saturated ammonium chloride solution was added to the reaction mixture. The solvent was distilled off. After extraction with ethyl acetate followed by drying over magnesium sulfate and concentration under reduced pressure, the residue was purified according to silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.27 g of the intended compound in the form of white crystals.

Workup

  1. distillationThe solvent was distilled off
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialby drying over magnesium sulfate and concentration under reduced pressure
  4. customthe residue was purified

Sources & evidence

ORD record
ord-6c61509ca7614129953489b875b0f1b7
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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