Hydroxyphenylacetic acid → Ethyl 4-hydroxyphenylacetate

HRID 846063Notes

Reaction equation

HRID 846063 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.[CH2:12](O)[CH3:13].O=S(Cl)Cl>C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 702EthanolHCID 24386Thionyl Chloride

Product 1

HCID 28310Ethyl 4-hydroxyphenylacetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-hydroxyphenylacetic acid (9.12 g, 0.06 mol), absolute ethanol (50 mL) and SOCl2 (2 mL, 0.028 mol) was refluxed for 3 hours. The residue was cooled, diluted with ethyl acetate (200 mL), washed first with dilute aqueous sodium bicarbonate (100 mL) and then twice with water (100 mL), then was dried over anhydrous MgSO4, filtered and evaporated in vacuo. Ethyl 4-hydroxyphenylacetate was obtained as an oil.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe residue was cooled
  3. washwashed first with dilute aqueous sodium bicarbonate (100 mL)
  4. dry with materialtwice with water (100 mL), then was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-2fa8286913bf437091aab85f0f0359cf
Source dataset
uspto-grants-1992_08
Patent number
US05135926

Reaction notes

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