Methanol → HCID 70224727, compound
Reaction equation
[CH:1]([C:4]1[C:5]([O:15][CH3:16])=[CH:6][C:7]([CH3:14])=[C:8]([CH2:10][C:11]([OH:13])=[O:12])[CH:9]=1)([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH3:21]O>>[CH:1]([C:4]1[C:5]([O:15][CH3:16])=[CH:6][C:7]([CH3:14])=[C:8]([CH2:10][C:11]([O:13][CH3:21])=[O:12])[CH:9]=1)([CH3:3])[CH3:2]Participants
Procedure
(5-Isopropyl-4-methoxy-2-methylphenyl)acetic acid (CAS No. 81354-65-6, 5.5 g) was dissolved in methanol (50 mL), and thionyl chloride (3.5 mL) was added dropwise under ice-cooling. After dropwise addition of the reagent, the mixture was brought back to room temperature and stirred for two hours. The reaction solution was concentrated under reduced pressure. A saturated sodium bicarbonate solution and tert-butyl methyl ether were added and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (5.0 g). The property values of the compound are as follows.
Workup
- temperaturecooling
- additionAfter dropwise addition of the reagent
- customwas brought back to room temperature
- concentrationThe reaction solution was concentrated under reduced pressure
- additionA saturated sodium bicarbonate solution and tert-butyl methyl ether were added
- customthe organic layer was separated
- washThe resulting organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customThe drying agent was separated by filtration
- concentrationthe organic layer was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-a1a86c113be242deb6e24dc6ec9ca864
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754100B2
Reaction notes
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