Ethanol → Ethyl 4-methylnicotinate
Reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>>[CH2:16]([O:9][C:8](=[O:10])[C:7]1[C:2]([CH3:1])=[CH:3][CH:4]=[N:5][CH:6]=1)[CH3:17]Participants
Procedure
To a flask containing 4-methylnicotinic acid 1.5 hydrochloride (9.6 g, 55.3 mmol), dissolved in dry absolute ethanol (120 mL) was added concentrated sulfuric acid (6 mL) via drop-wise addition. The material was heated to reflux temperature and stirred over night. The flask was cooled to ambient and about 85% of the solvent was removed on the rotovap. Ethyl acetate (40 mL) was added and the material was basified via drop-wise addition of an aqueous saturated sodium bicarbonate solution. Ethyl acetate (40 mL) and water (20 mL) was added and the material was shaken in a separatory funnel. The ethyl acetate phase was collected and washed with brine (60 mL). The aqueous phases were back extracted with ethyl acetate (2×50 mL), the organic phases were combined, dried (MgSO4), filtered and stripped affording ethyl-4-methylnicotinoate as a brown mobile oil. MS (M+H)+=166.
Workup
- additionvia drop-wise addition
- temperatureThe material was heated
- temperatureto reflux temperature
- customwas removed on the rotovap
- additionEthyl acetate (40 mL) was added
- additionthe material was basified via drop-wise addition of an aqueous saturated sodium bicarbonate solution
- additionEthyl acetate (40 mL) and water (20 mL) was added
- stirringthe material was shaken in a separatory funnel
- customThe ethyl acetate phase was collected
- washwashed with brine (60 mL)
- extractionThe aqueous phases were back extracted with ethyl acetate (2×50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-7887f93a55184f708577a0ed3a00c310
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08361962B2
Reaction notes
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