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

HRID 1374840Notes

Reaction equation

HRID 1374840 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].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:17][CH3:18])=[O:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11970(2-Hydroxyphenyl)acetic acid

Product 1

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

Procedure

2-Hydroxyphenylacetic acid (6.06 g, 39.8 mmol) was dissolved in ethanol (180 ml) and the solution was added with concentrated sulfuric acid (2 ml) and heated under reflux for 90 minutes. The reaction mixture was concentrated under reduced pressure and diluted with ethyl acetate. The mixture was washed with water and saturated brine, and dried over sodium sulfate. Insoluble solids were removed by filtration, and the filtrate was concentrated under reduced pressure to obtain the title compound as orange oil (7.67 g, yield: quantitative).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 90 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiondiluted with ethyl acetate
  5. washThe mixture was washed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customInsoluble solids were removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6e706c0e88234beba220121988e30e0a
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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