Acetone → 4-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-but-3-en-2-one

HRID 1160299Notes

Reaction equation

HRID 1160299 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH:9]=[CH:8][C:5]=1[CH:6]=O.Cl.[CH3:22][C:23]([CH3:25])=[O:24]>O>[CH3:3][C:4]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH:9]=[CH:8][C:5]=1[CH:6]=[CH:22][C:23](=[O:24])[CH3:25]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866024602-Methyl-4-(2-methyl-benzyloxy)-benzaldehyde

Product 1

HCID 686742184-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-but-3-en-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2N NaOH(aq) (0.6 mL) was added to a solution of 31.3 (100 mg, 0.42 mmol) in acetone (1 mL). The reaction was stirred at room temperature overnight and then taken up in water. The aqueous solution was acidified with 1N HCl(aq) (1.5 mL) and extracted with ethyl acetate. The organic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The resultant residue was purified via radial chromatography (20% ethyl acetate in hexanes) to yield 74 mg (63%) of 4-[2-Methyl-4-(2-methyl-benzyloxy)-phenyl]-but-3-en-2-one (31.4). LC/MSD m/e: 281.4 (M+H); 1H NMR (400 MHz) (acetone-d6) δ 7.83 (1H, d, J=16), 7.70 (1H, m), 7.46 (1H, m), 7.25 (3H, m), 6.96 (2H, m), 6.63 (1H, d, J=16 Hz).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified via radial chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-19a26eb2fd394e36a454915bbff02918
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

Loading…