Phenylacetic Acid → Tert-butyl 2-phenylacetate

HRID 1771952Notes

Reaction equation

HRID 1771952 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 68%

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) stirred at room temperature for 20 hours. The solution was transferred very slowly to stirred mixture of saturated aqueous NaHCO3 and Et2O. Extensive bubbling was observed. 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, Intermediate S5A (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
  4. customExtensive bubbling
  5. customThe resulting layers were separated
  6. washthe organic layer washed with saturated aqueous NaHCO3
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a13b233684f34c0c9b69195d5f126035
Source dataset
uspto-grants-2016_02
Patent number
US09249157B2

Reaction notes

Loading…