1-Bromopropane → (6-Methyl-1,3-benzodioxol-5-yl)butan-1-ol

HRID 2259787Notes

Reaction equation

HRID 2259787 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][CH2:16][CH3:17].[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:15][CH2:16][CH3:17])=[CH:6][C:5]2[O:10][CH2:11][O:12][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 25517Ammonium ChlorideHCID 31462426-Methyl-2H-1,3-benzodioxole-5-carbaldehydeHCID 5462224Magnesium

Product 1

HCID 67784687(6-Methyl-1,3-benzodioxol-5-yl)butan-1-olYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.0 g of (6-methyl-1,3-benzodioxol-5-yl)-carboxaldehyde in 20 ml of tetrahydrofuran was dropwise added at a room temperature to a Grignard reagent prepared from 0.86 g of magnesium ribbon, 10 ml of tetrahydrofuran and 4.4 g of 1-bromopropane. The obtained mixture was stirred at a room temperature for one hour, followed by the addition of a saturated aqueous solution of ammonium chloride. The obtained mixture was extracted with ether. The organic layer was washed with an aqueous solution of common salt, dried over magnesium sulfate and distilled to remove the solvent. 5.6 g of (6-methyl-1,3-benzodioxol-5-yl)-butan-1-ol was obtained.

Workup

  1. extractionThe obtained mixture was extracted with ether
  2. washThe organic layer was washed with an aqueous solution of common salt
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled
  5. customto remove the solvent

Sources & evidence

ORD record
ord-57841c14520a4e6199eeea86e81e90e0
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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