3',4'-Methylenedioxymandelic acid → 1,2-Ethanediol, 1-(1,3-benzodioxol-5-yl)-

HRID 2177046Notes

Reaction equation

HRID 2177046 reaction equation
[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7](O)=[O:8])=[CH:4][C:3]=2[O:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[O:14]1[C:13]2[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[CH2:7][OH:8])=[CH:4][C:3]=2[O:2][CH2:1]1

Participants

4

Reactant 2

HCID 1196183',4'-Methylenedioxymandelic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 149198181,2-Ethanediol, 1-(1,3-benzodioxol-5-yl)-Yield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3,4-(methylenedioxy)mandelic acid (1.5 g, 7.65 mmol) in tetrahydrofuran was added lithium aluminum hydride (0.58 g, 15.29 mmol). The reaction mixture was refluxed for 1.5 hours. The reaction mixture was cooled (0° C.), quenched with sat, ammonium chloride solution, filtered, concentrated to yield 1.3 g of 1-benzo[1,3]dioxol-5-yl-ethane-1,2-diol.

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 hours
  2. customquenched
  3. filtrationammonium chloride solution, filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-53d76e3d0af543e398f85ede967e13e3
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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