Hydrochloric Acid → HCID 86673383, compound

HRID 1023345Notes

Reaction equation

HRID 1023345 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)C.Cl.[OH-].[Na+]>C1COCC1>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13]/[CH:12]=[CH:11]/[C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67353800HCID 67353800, compound

Product 1

HCID 86673383HCID 86673383, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(diethoxymethyl)-4-[(E)-3-(4-methylphenoxy)prop-1-en-1-yl]benzene (1.270 g) in THF (20 mL) was added 6 M HCl (4 mL) at room temperature. The mixture was stirred at room temperature for 0.5 hour. To the mixture was added 5 M NaOH (4 mL), and the mixture was evaporated under reduced pressure. To the residue was added saturated aqueous NaHCO3, and the mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 4-[(E)-3-(4-methylphenoxy)prop-1-en-1-yl]benzaldehyde (0.942 g) as a colorless solid.

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. additionTo the residue was added saturated aqueous NaHCO3
  3. extractionthe mixture was extracted with AcOEt
  4. washThe organic layer was washed with saturated aqueous NaCl
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b054c27dceb42ddad7b9e035580055f
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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