Hydroxyphenylacetic acid → Ethyl 4-hydroxyphenylacetate

HRID 1292109Notes

Reaction equation

HRID 1292109 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:12]1(C)C=CC=C[CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(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 1140TolueneHCID 6101p-Toluenesulfonic acid

Product 1

HCID 28310Ethyl 4-hydroxyphenylacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixed solution comprising 4-hydroxyphenylacetic acid (150.0 g), toluene (250 ml), ethanol (150 ml), and p-toluenesulfonic acid (50 g) was refluxed with stirring for 3 hours. The reaction mixture was washed with aqueous sodium hydrogencarbonate solution, dried over sodium sulfate anhydride, and then concentrated under a vacuum to yield 164.3 g of oily ethyl 4-hydroxyphenylacetate. This material was subjected to a reaction identical to that of Reference Example 1, thereby yielding 138.2 g of oily ethyl 4-hydroxy-3-methallylphenylacetate. In a manner identical to Reference Examples 2 and 3, this material was successively subjected to catalytic reduction, benzylation, and hydrolysis reactions, thereby yielding 70.4 g of 4-benzyloxy-3-isobutylphenylacetic acid. As in the case of Example 3, this material (1.0 g) was subjected to a condensation reaction with 1-isobutylpiperazine (0.48 g), thereby yielding 1.3 g of the aimed compound.

Workup

  1. washThe reaction mixture was washed with aqueous sodium hydrogencarbonate solution
  2. dry with materialdried over sodium sulfate anhydride
  3. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-7391a65e8d9e4de6a58dad1714716fcd
Source dataset
uspto-grants-1998_05
Patent number
US05756505

Reaction notes

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