Acetone → 4-(3-Methoxy-2,4,6-trimethylphenyl)but-3-en-2-one

HRID 1382165Notes

Reaction equation

[OH-].[Na+].[CH3:3][O:4][C:5]1[C:6]([CH3:15])=[C:7]([C:10]([CH3:14])=[CH:11][C:12]=1[CH3:13])[CH:8]=O.[CH3:16][C:17]([CH3:19])=[O:18]>O>[CH3:3][O:4][C:5]1[C:6]([CH3:15])=[C:7]([CH:8]=[CH:16][C:17](=[O:18])[CH3:19])[C:10]([CH3:14])=[CH:11][C:12]=1[CH3:13]

Participants

Conditions

Temperature: 65 °C

Procedure

An aqueous solution of 2% sodium hydroxide (16.5 ml) was added dropwise over a period of 5 minutes to a suspension of 3-methoxy-2,4,6-trimethylbenzaldehyde (23.5 g) in acetone (21.3 g) and water (13 ml). The mixture was stirred at a temperature of 65° C. for a period of 4 hours and then extracted with dichloromethane. The organic extract was washed several times with water, dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure. The product, 1-(3-methoxy-2,4,6-trimethylphenyl)but-1-en-3-one, was obtained as a viscous oil (28.0 g). Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 2.25 (6H, s); 2.36 (3H, s); 3.67 (3H, s); 6.27 (1H, d); 7.16 (1H, s); 7.61 (1H, d).

Workup

extractionextracted with dichloromethane
extractionThe organic extract
washwas washed several times with water
dry with materialdried over anhydrous sodium sulfate
customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record: ord-e7c2b379b1124562b30e03233426a8de
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04806141

Reaction notes

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