Iodoethane → 1-(2H-1,3-Benzodioxol-5-yl)propan-1-ol

HRID 2039443Notes

Reaction equation

HRID 2039443 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=2[O:2]1.[Mg].I[CH2:14][CH3:15].[Cl-].[NH4+]>C(OCC)C.O>[CH2:1]1[O:11][C:10]2[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH2:14][CH3:15])=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8438PiperonalHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 1655531-(2H-1,3-Benzodioxol-5-yl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3,4-methylenedioxybenzaldehyde (4.5 g, 30 mmol) of formula 2 prepared in dry diethyl ether is slowly added to an ethereal solution of Grignard reagent prepared from magnesium metal (0.84 g, 35 mmol) and iodoethane (3.0 ml, 40 mmol) and the contents stirred for 1 hour at room temperature. After the completion of the reaction, the mixture is processed by adding saturated aqueous solution of ammonium chloride (10 ml) followed by dilution with water (100 ml), separating the organic layer and extracting the aqueous layer with solvent ether (2×100 ml). The combined organic layer washed with water (2×20 ml) dried over anhydrous sodium sulfate and concentrated in vacuo to yield 1-(3,4-methylenedioxyphenyl) propan-1-ol, a semisolid of formula 3 (5.3 g, 97.5%).

Workup

  1. customAfter the completion of the reaction
  2. customseparating the organic layer
  3. extractionextracting the aqueous layer with solvent ether (2×100 ml)
  4. washThe combined organic layer washed with water (2×20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fecffbeec75482a8a31938c04cd2329
Source dataset
uspto-grants-2013_11
Patent number
US08580752B2

Reaction notes

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