Sulfuric Acid → Tert-butyl 4-cyanobenzoate
Reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].S(=O)(=O)(O)O.[CH2:17]=[C:18]([CH3:20])[CH3:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:18]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)([CH3:20])([CH3:19])[CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In 612 ml of methylene chloride was suspended 45.0 g of 4-cyanobenzoic acid and 3.1 ml of conc. sulfuric acid. To the suspension was added, while stirring at 0° C., 310 ml of isobutene. The mixture was stirred for 13 days. The reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The resulting precipitate was collected by filtration and washed with hexane. The filtrate and the washings were combined and concentrated under reduced pressure. The concentrate was purified by silica gel chromatography (hexane/ethyl acetate=10/1), followed by crystallization from methylene chloride/petroleum ether to afford 43.1 g of the title compound as a white crystalline product.
Workup
- additionTo the suspension was added
- stirringThe mixture was stirred for 13 days
- extractionextracted with ethyl acetate
- concentrationThe organic layer was concentrated under reduced pressure
- filtrationThe resulting precipitate was collected by filtration
- washwashed with hexane
- concentrationconcentrated under reduced pressure
- customThe concentrate was purified by silica gel chromatography (hexane/ethyl acetate=10/1)
- customfollowed by crystallization from methylene chloride/petroleum ether
Sources & evidence
- ORD record
- ord-8d773e051128425d8a4e75220f723c49
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05876756
Reaction notes
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