Water → 2-(Benzo[d][1,3]dioxol-5-yl)propan-2-ol

HRID 1195298Notes

Reaction equation

HRID 1195298 reaction equation
[CH3:1][Li].[C:3]([C:6]1[CH:14]=[CH:13][C:9]2[O:10][CH2:11][O:12][C:8]=2[CH:7]=1)(=[O:5])[CH3:4].O>CCOCC.O1CCCC1>[O:10]1[C:9]2[CH:13]=[CH:14][C:6]([C:3]([OH:5])([CH3:1])[CH3:4])=[CH:7][C:8]=2[O:12][CH2:11]1

Participants

6

Reactant 3

HCID 962WaterHCID 76622AcetopiperoneHCID 178418348HCID 178418348, compound

Product 1

HCID 118196322-(Benzo[d][1,3]dioxol-5-yl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

About 600 ml of a 1.5 M solution of methyllithium in ether was added to 500 ml of tetrahydrofuran to obtain a mixture. A suspension of 93.45 g of 5-acetyl-1,3-benzodioxole in 900 ml of tetrahydrofuran was added to the mixture, while keeping it at -20° C. by cooling and the obtained mixture was stirred as such for one hour. Water was added to the reaction mixture and the obtained mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of common salt and dried over anhydrous magnesium sulfate. The resulting mixture was filtered and the filtrate was concentrated to obtain 97 g of the title compound as an oil.

Workup

  1. customto obtain a mixture
  2. additionwas added to the mixture
  3. customat -20° C.
  4. temperatureby cooling
  5. extractionthe obtained mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe resulting mixture was filtered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b2a15f4325de4fcca90a9f20fbe48148
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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