Methanol → Methyl 2-(2-methylphenyl)acetate
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].S(=O)(=O)(O)O.[CH3:17]O>>[C:2]1([CH3:1])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:17])=[O:10]Participants
Procedure
To a flask (1000 mL), 120 g of 2-methylphenylacetic acid and 400 mL of anhydrous methanol were added, and then 24 mL of concentrated sulfuric acid was further added with stiffing. The mixture was heated with an oil bath and refluxed. The reaction was monitored with thin layer chromatography (TLC) until the reactants were basically consumed. Subsequently, the solvent was removed by vacuum distillation. The residue was dumped into 400 mL of water and extracted with 400 mL of ethyl acetate. The organic layer was washed with water (2×200 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A light yellow oily product was obtained. The light yellow oily product was further distilled under vacuum condition to yield 117.3 g of a colorless oily product (135-140° C., 16 mmHg) with a yield of 92%.
Workup
- temperatureThe mixture was heated with an oil bath
- temperaturerefluxed
- customwere basically consumed
- customSubsequently, the solvent was removed by vacuum distillation
- extractionextracted with 400 mL of ethyl acetate
- washThe organic layer was washed with water (2×200 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customA light yellow oily product was obtained
- distillationThe light yellow oily product was further distilled under vacuum condition
Sources & evidence
- ORD record
- ord-11f8299135eb409698e764058199d918
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422254B2
Reaction notes
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