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

HRID 1364468Notes

Reaction equation

HRID 1364468 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 with sat. ammonium chloride solution
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-36de6005e1ff4627bc69c9ee1ca499fe
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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