Toluene → HCID 59224662, compound
Reaction equation
[I:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13]1([CH3:19])[CH:18]=CC=C[CH:14]=1>C(OCC)(=O)C>[C:13]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([I:1])[C:3]([CH3:12])=[CH:4][C:5]=1[CH3:11])([CH3:19])([CH3:18])[CH3:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
5-Iodo-2,4-dimethylbenzoic acid (4.5 g, 16.3 mmol) obtained in Step 1 above was placed in a reaction vessel, and then anhydrous toluene (10 ml) and N,N-dimethylformamide/di-tert-butyl acetal (25 ml) were added thereto. The resulting mixture was stirred at 80° C. for 2 hours. The reaction solution was diluted with ethyl acetate (300 ml), and washed three times with a saturated aqueous sodium bicarbonate solution (100 ml), twice with water (100 ml), and once with a saturated aqueous sodium chloride solution (100 ml). The washed ethyl acetate solution was dried over anhydrous sodium sulfate (50 g). After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=10:1) to yield 5-iodo-2,4-dimethylbenzoic acid tert-butyl ester (3.8 g) as a white solid material.
Workup
- washwashed three times with a saturated aqueous sodium bicarbonate solution (100 ml)
- dry with materialThe washed ethyl acetate solution was dried over anhydrous sodium sulfate (50 g)
- filtrationAfter filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=10:1)
Sources & evidence
- ORD record
- ord-ec5b93e6573e4a67b0415379d1288a88
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362236B2
Reaction notes
Loading…