Isopropyl iodide → Methyl 3-formyl-4-isopropoxybenzoate
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH:21]([CH3:23])[CH3:22]>CN(C)C=O>[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:21]([CH3:23])[CH3:22])[C:6]([O:8][CH3:9])=[O:7])=[O:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To methyl 3-formyl-4-hydroxy-benzoate (10.0 g, 55.5 mmol), potassium carbonate (30.7 g, 222 mmol) and N,N-dimethylformamide (63 mL) was added 2-iodopropane (11.1 mL, 111 mmol). The mixture was heated at 60° C. for 18 hours. The mixture was filtered using ethyl acetate (200 mL) and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and was washed with water (3×75 mL) and a saturated aqueous solution of sodium chloride (1×75 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield methyl 3-formyl-4-isopropoxy-benzoate (98%) as a yellow viscous liquid. ESI-MS m/z calc. 222.2. found 223.3 (M+1)+; Retention time: 1.51 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 10.35 (s, 1H), 8.23 (d, J=2.3 Hz, 1H), 8.17 (dd, J=8.8, 2.3 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 4.98-4.83 (m, 1H), 3.85 (s, 3H), 1.38 (d, J=6.0 Hz, 6H).
Workup
- filtrationThe mixture was filtered
- customthe solvent was evaporated under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate (150 mL)
- washwas washed with water (3×75 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-cbca694baf2b44deacdb1085928b8704
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598164B2
Reaction notes
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