Sulfuric Acid → Tert-butyl 4-cyanobenzoate

HRID 376537Notes

Reaction equation

HRID 376537 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

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 120874-Cyanobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 271408Tert-butyl 4-cyanobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In 612 ml of methylene chloride were 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 hydrogencarbonate, which was subjected to extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. Resulting precipitate was collected by filtration and washed with hexane. The filtrate and the washing were combined, which was concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (hexane/ethyl acetate=10/1), followed by crystallization from methylene chloride/petroleum ether to afford 43.1 g of the titled compound as a white crystalline product.

Workup

  1. additionTo the suspension was added
  2. stirringThe mixture was stirred for 13 days
  3. extractionwas subjected to extraction with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customResulting precipitate
  6. filtrationwas collected by filtration
  7. washwashed with hexane
  8. concentrationwhich was concentrated under reduced pressure
  9. customThe concentrate was purified by means of a silica gel chromatography (hexane/ethyl acetate=10/1)
  10. customfollowed by crystallization from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-db4415321d3d48c49f6bcf1c654255db
Source dataset
uspto-grants-2000_02
Patent number
US06020334

Reaction notes

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