Phenylacetic Acid → Tert-butyl 2-phenylacetate

反応式

[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

参加物

反応物 5

HCID 999Phenylacetic Acid

HCID 3283Diethyl Ether

HCID 10908tert-Butyl acetate

HCID 24247Perchloric Acid

HCID 516892Sodium Bicarbonate

生成物 1

HCID 316203Tert-butyl 2-phenylacetate収率 68%

実験手順

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).