3'-Hydroxyphenylacetic acid → Ethyl (3-Hydroxyphenyl)acetate

HRID 1925228Notes

Reaction equation

HRID 1925228 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.O.[C:13]1(C)C=CC(S(O)(=O)=O)=C[CH:14]=1>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:13][CH3:14])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 121223'-Hydroxyphenylacetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 572437Ethyl (3-Hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-Hydroxyphenylacetic acid (25 g, 164.31 mmol) and p-Toluenesulfonic acid monohydrate (3.49 g, 18.3 mmol) in abs ethanol (250 ml) was refluxed for 4 hours or until all the starting material is consumed. The reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound.

Workup

  1. customis consumed
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-7b9c74aeedb64a9cacfc145d8a171641
Source dataset
uspto-grants-2012_05
Patent number
US08178675B2

Reaction notes

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