(2-Hydroxyphenyl)acetic acid → 2-(2-Hydroxyphenyl)acetic acid ethyl ester

HRID 516842

Reaction equation

HRID 516842 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].O.[C:13]1(C)C=CC(S(O)(=O)=O)=C[CH:14]=1>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:13][CH3:14])=[O:10]

Participants

4

Reactant 2

HCID 11970(2-Hydroxyphenyl)acetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 5210752-(2-Hydroxyphenyl)acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The stirred solution of 2-(2-Hydroxyphenyl)acetic acid (10 g, 65.7 mmol) and p-Toluenesulfonic acid monohydrate (1.40 g, 7.3 mmol) in abs ethanol (100 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 1M HCl and brine. 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 1M HCl and brine
  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-b35772130c7d4cfaabad735d4e2e9533
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Linked notes

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