Acetone → 4-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one

HRID 77674Notes

Reaction equation

HRID 77674 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[O:13][CH3:14].[CH3:15][C:16]([CH3:18])=[O:17].[OH-].[Na+].O>C(O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:15][C:16](=[O:17])[CH3:18])=[CH:7][C:6]=1[O:13][CH3:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 796613-Methoxy-4-(methoxymethoxy)benzaldehyde

Product 1

HCID 695016824-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-oneYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methoxymethyloxy-3-methoxybenzaldehyde (1j, 2.30 g, 11.7 mmol) and acetone (19, 8.75 ml, 118.4 mmol) were combined in ethanol (20 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (0.80 g, 20.0 mmol) and water (20 ml) was added and the mixture stirred for 1 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from hexane to give 2.70 g (97%) of a white solid: mp 73-75° C.; 1H NMR: δ 2.34 (s, 3H), 3.48 (s, 3H), 3.89 (s, 3H), 5.24 (s, 2H), 6.58 (d, 1H, J=16.1 Hz), 7.07 (m, 2H), 7.13 (d, 1H, J=8.7 Hz), 7.43 (d, 1H, J=16.1 Hz); 13C NMR: δ 27.4, 55.9, 56.3, 95.2, 110.4, 115.9, 122.5, 125.7, 128.7, 143.1, 148.7, 149.8, 198.0.

Workup

  1. stirringthe mixture stirred for 1 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was recrystallized from hexane

Sources & evidence

ORD record
ord-118d78be12f44474bf68d3fd5355aca4
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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