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

HRID 2177045Notes

Reaction equation

HRID 2177045 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-585f03b05cae478daf8b3fa7b7192836
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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