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

HRID 2106044Notes

Reaction equation

HRID 2106044 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, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (−78° C.) solution of 10 g of benzo[1,3]dioxole4-carbaldehyde in 200 mL of THF was added by addition funnel 43.7 mL of a 1.6M MeLi solution in diethyl ether. The reaction was slowly warmed to room temperature and stirred overnight. The reaction was monitored by TLC. The mixture was then cooled to −78° C. and quenched with saturated aqueous ammonium chloride and concentrated in vacuo. The residue was extracted with EtOAc. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give 11 g of 1-benzo[1,3]dioxol-4-ylethanol as a brown oil that crystallized upon standing.

Workup

  1. temperatureThe mixture was then cooled to −78° C.
  2. customquenched with saturated aqueous ammonium chloride
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1eaefc1c55374f23a7519cdfabb5af79
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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