Hydroxyphenylacetic acid → Ethyl 4-hydroxyphenylacetate

HRID 1458297Notes

Reaction equation

HRID 1458297 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.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:22](O)[CH3:23]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:22][CH3:23])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 28310Ethyl 4-hydroxyphenylacetate

Procedure

To a solution of 4- hydroxyphenylacetic acid (3.00 g) in ethanol (50 ml) was added sulfuric acid (5 ml). The mixture was refluxed with heating for 4 hours. Aqueous sodium bicarbonate solution was added to the reaction solution so as to make basic. Then, the reaction solution was extracted with chloroform. The extract was dried over sodium sulfate anhydride and then concentrated under a vacuum to yield a raw product of ethyl 4-hydroxyphenylacetate. In a manner similar to Reference Example 1, this raw product was reacted with geranyl bromide (7.10 g) and then hydrolyzed to yield 3.54 g (61%) of 4-geranylophenylacetic acid.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 4 hours
  3. extractionThen, the reaction solution was extracted with chloroform
  4. dry with materialThe extract was dried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-7009ba8b364d4a37ba1d20c66ece0740
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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