1,3-Benzodioxole-4-carboxaldehyde → HCID 10103506, compound

HRID 400648Notes

Reaction equation

HRID 400648 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]=[O:11])[C:4]=2[O:3][CH2:2]1.[Li][CH3:13]>C1COCC1.C(OCC)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]([OH:11])[CH3:13])[C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 822641,3-Benzodioxole-4-carboxaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 10103506HCID 10103506, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzo[1,3]dioxole-4-carbaldehyde (10 g, 66.7 mmol) in 200 mL THF at −78° C. was added, via addition funnel, 43.7 mL of a 1.6 M MeLi solution in diethyl ether. The reaction was slowly warmed to room temperature and stirred overnight. A TLC of an aliquot showed reaction was complete. The reaction was then cooled to −78° C. and quenched with saturated aqueous ammonium chloride and concentrated in vacuo. The residue was then extracted with ethyl acetate. The organics were combined, dried over magnesium sulfate, and concentrated in vacuo to give 11 g (99.4% yield) of 1-benzo[1,3]dioxol-4-ylethanol as a brown oil that crystallized upon standing.

Workup

  1. customreaction
  2. temperatureThe reaction was then cooled to −78° C.
  3. customquenched with saturated aqueous ammonium chloride
  4. concentrationconcentrated in vacuo
  5. extractionThe residue was then extracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d73055e509c14a5989f8778c813d472a
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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