Ethanol → Ethyl 3-(3-hydroxyphenyl)propanoate

HRID 1925234Notes

Reaction equation

HRID 1925234 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])C(O)=O)[CH:5]=[CH:6][CH:7]=1.[OH2:13].[C:14]1([CH3:24])C=CC(S(O)(=O)=O)=CC=1.[CH2:25]([OH:27])C>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:12][C:25]([O:27][CH2:14][CH3:24])=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 124468532-(3-Hydroxyphenyl)propionic acid, (+-)-

Product 1

HCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoate

Procedure

A solution of 3-Hydroxyphenylpropanoic acid (25 g, 150.60 mmol) and p-Toluenesulfonic acid monohydrate (3.80 g, 20 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-20b135e5414c4a0c9a10063968dc63f0
Source dataset
uspto-grants-2012_05
Patent number
US08178675B2

Reaction notes

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