Phenylacetic Acid → Tert-butyl 2-phenylacetate

HRID 714235Notes

Reaction equation

HRID 714235 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([O-])(O)=O.[Na+].CCOCC.[C:26](OC(C)=O)([CH3:29])([CH3:28])[CH3:27]>>[C:1]1([CH2:7][C:8]([O:10][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 999Phenylacetic AcidHCID 3283Diethyl EtherHCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 316203Tert-butyl 2-phenylacetateYield 68%

Procedure

A solution of 2-phenylacetic acid (12 g, 88 mmol) in t-BuOAc (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. Gas evolution was observed. The resulting layers were separated and the organic layer was washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and concentrated to give Intermediate S-3D (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. stirringto stirred
  2. customThe resulting layers were separated
  3. washthe organic layer was washed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give Intermediate S-3D (11.6 g, 68% yield)

Sources & evidence

ORD record
ord-444366aa28c1440b9d32be6bdde5c003
Source dataset
uspto-grants-2015_11
Patent number
US09187434B2

Reaction notes

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