Phenylacetic Acid → Tert-butyl 2-phenylacetate

HRID 2276875Notes

Reaction equation

HRID 2276875 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl(O)(=O)(=O)=O>C(OC(C)=O)(C)(C)C>[C:1]1([CH2:7][C:8]([O:10][C:1]([CH3:7])([CH3:6])[CH3:2])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 999Phenylacetic AcidHCID 24247Perchloric Acid

Product 1

HCID 316203Tert-butyl 2-phenylacetateYield 137.1%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A solution of 2-phenylacetic acid (12 g, 88 mmol) in tBuOAc (250 mL) in a 1 L round-bottomed flask was treated with perchloric acid, 70% redistilled (0.212 mL, 3.53 mmol), and stirred at room temperature for 20 hours. The solution was transferred very slowly to stirred mixture of saturated aqueous NaHCO3 and Et2O, which resulted in bubbling. The resulting layers were separated and the organic layer washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and concentrated to give tert-butyl 2-phenylacetate (11.6 g, 68% yield). 1H NMR (500 MHz, chloroform-d) δ 7.34-7.29 (m, 2H), 7.28-7.22 (m, 3H), 3.52 (s, 2H), 1.44 (s, 9H).

Workup

  1. distillationredistilled (0.212 mL, 3.53 mmol)
  2. stirringto stirred
  3. additionmixture of saturated aqueous NaHCO3 and Et2O, which
  4. customresulted
  5. customin bubbling
  6. customThe resulting layers were separated
  7. washthe organic layer washed with saturated aqueous NaHCO3
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4499a57caa764e0e80fc0895cd5edec7
Source dataset
uspto-grants-2015_09
Patent number
US09133139B2

Reaction notes

Loading…