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

HRID 1195316Notes

Reaction equation

HRID 1195316 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. extractionwas 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-59d1036511d445a7b7d91d6e227d0509
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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