Hydrochloric Acid → 3-(4-Acetyl-2-methylphenyl)acrylic acid

HRID 1951602Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11](Br)[C:12]([O:14]C)=[O:13])=[C:6]([CH3:17])[CH:5]=1)(=[O:3])[CH3:2].C[O-].[Na+].Cl.O>CO>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([OH:14])=[O:13])=[C:6]([CH3:17])[CH:5]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 5 °C

Procedure

The obtained methyl 3-(4-acetyl-2-methylphenyl)-2-bromopropionate (2.79 g, 9.33 mmol) was dissolved in methanol (80 mL). The solution was cooled to 5° C. Sodium methoxide (1.51 g, 27.98 mmol) was added to the solution. The mixture was stirred at room temperature for 20 minutes, refluxed for 1 hour, cooled to room temperature, and acidized with 1N hydrochloric acid. Water (50 mL) was added to the mixture. The mixture was extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 657 mg of the desired compound as yellow crystalline product (yield 34%).

Workup

temperaturerefluxed for 1 hour
temperaturecooled to room temperature
extractionThe mixture was extracted with chloroform
dry with materialThe organic layer was dried with anhydrous sodium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-2777a7ee417c45a6bb069cf8a41faccc
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404726B2

Reaction notes

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