Sodium Hydroxide → Piperonyl alcohol

HRID 351821Notes

Reaction equation

HRID 351821 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]1[O:20][C:19]2[CH:18]=[CH:17][C:11]([C:12](OCC)=[O:13])=[CH:10][C:9]=2[O:8]1.[OH-].[Na+]>CCOCC.O.C1COCC1>[CH2:7]1[O:8][C:9]2[CH:10]=[C:11]([CH2:12][OH:13])[CH:17]=[CH:18][C:19]=2[O:20]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 81391Ethyl 1,3-benzodioxole-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10322Piperonyl alcoholYield 94.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.99 g (26.16 mmol) of LiAlH4 and 80 mL of Et2O, 2.54 g (13.08 mmol) of ethyl 3,4-(methylenedioxy)benzoate (obtained in the preceding section) dissolved in 160 mL of Et2O was added under argon, and the mixture was stirred overnight at room temperature. A mixture of 1.62 mL of H2O and 3.41 mL of THF, followed by 1.62 mL of 15% NaOH and then 4.43 mL of H2O were added dropwise. The resulting mixture was filtered, washed with Et2O and EtOAc, and the solvent was evaporated. The residue was partitioned between H2O and EtOAc, the layers were separated, the aqueous phase was extracted with EtOAc and the combined organic phases were dried over MgSO4 and concentrated, yielding 1.88 g of the desired product (94% yield).

Workup

  1. customobtained in the preceding section)
  2. additionwas added under argon
  3. filtrationThe resulting mixture was filtered
  4. washwashed with Et2O and EtOAc
  5. customthe solvent was evaporated
  6. customThe residue was partitioned between H2O and EtOAc
  7. customthe layers were separated
  8. extractionthe aqueous phase was extracted with EtOAc
  9. dry with materialthe combined organic phases were dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5b8d4825516c4a4c904b4cdf4816d49f
Source dataset
uspto-grants-2004_06
Patent number
US06743816B2

Reaction notes

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