Hydroxyphenylacetic acid → Tert-butyl 2-(4-hydroxyphenyl)acetate

HRID 1935759Notes

Reaction equation

HRID 1935759 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(OCC)(=O)C.[C:18]1([CH3:24])[CH:23]=CC=C[CH:19]=1>CCCCCC>[C:18]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)([CH3:24])([CH3:23])[CH3:19]

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 1140TolueneHCID 8857Ethyl Acetate

Product 1

HCID 15932404Tert-butyl 2-(4-hydroxyphenyl)acetateYield 56%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of 4-hydroxy-phenyl acetic acid (0.152 g, 1 mmol) in anhydrous toluene (5 mL) was heated at 80° C. and N,N-dimethyl formamide-di-ti-butyl acetal (1 mL, 4.17mmol) was added when the solution became homogenous. After 0.5 h, the reaction mixture was cooled to ambient temperature and the volatiles were distilled off in vacuo. The residue was diluted with water and extracted with diethyl ether (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 16% ethyl acetate in hexane as the eluent to afford the title compound as a solid (0.11 g, 56%).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. distillationthe volatiles were distilled off in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with diethyl ether (×2)
  5. extractionThe combined organic extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto afford an oil which

Sources & evidence

ORD record
ord-5ced73dcd79c4c9bbd6145c7fe67d1b8
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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