Methyl iodide → Ortho-formylphenylacetic acid
Reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])(O)=O.[C:12](=O)([O-:14])[O-:13].[K+].[K+].CI>CC(C)=O>[C:12]([CH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([OH:14])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 56 °C
Procedure
2-Carboxybenzaldehyde (4.53 g, 30 mmoles) was dissolved in acetone (100 mls) and anhydrous potassium carbonate (4.14 g, 30 mmoles) was added. After stirring methyl iodide (5.6 mls, 90 mmoles) was added and the reaction was heated (56° C.) for 30 minutes. The reaction became very thick so further acetone was added (50 mls) and stirring continued at room temperature for a further 72 hours. The reaction mixture was filtered through Celite and then evaporated to leave a viscous oil. The oil was then partitioned between water (30 ml) and ethyl acetate (30 ml). The aqueous layer was washed with further ethyl acetate (2×30 mls) and all the ethyl acetate extracts combined and washed with brine (30 mls) and then water (30 mls) dried over anhydrous magnesium sulphate and evaporated to leave a clear light yellow oil (4.9 g, 100% yield).
Workup
- additionwas added
- additionwas added (50 mls)
- filtrationThe reaction mixture was filtered through Celite
- customevaporated
- customto leave a viscous oil
- customThe oil was then partitioned between water (30 ml) and ethyl acetate (30 ml)
- washThe aqueous layer was washed with further ethyl acetate (2×30 mls) and all the ethyl acetate
- washwashed with brine (30 mls)
- dry with materialwater (30 mls) dried over anhydrous magnesium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-95265bcc98e24992b2b297b137ee141f
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716302B2
Reaction notes
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