Ethanol → Ethyl (3-Hydroxyphenyl)acetate

HRID 1078697Notes

Reaction equation

HRID 1078697 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:17][CH3:18])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 121223'-Hydroxyphenylacetic acid

Product 1

HCID 572437Ethyl (3-Hydroxyphenyl)acetateYield 98%

Procedure

A mixture of 100 g (0.658 mol) of 3-hydroxyphenylacetic acid, 6.0 ml concentrated sulfuric acid and 800 ml of ethanol was refluxed through a soxhlet with 3A molecular sieves for 3 hours. The reaction was cooled and concentrated to an oil on a rotovapor. The residue was added to 500 ml ice cold saturated sodium bicarbonate and 1 liter of ether. The ether extract was dried over magnesium sulfate and evaporated to give 116 g (98%) of ethyl 3-hydroxyphenylacetate as an oil.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated to an oil on a rotovapor
  3. additionThe residue was added to 500 ml ice cold saturated sodium bicarbonate and 1 liter of ether
  4. extractionThe ether extract
  5. dry with materialwas dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0966284537ed45c2b54df068a5cf5a31
Source dataset
uspto-grants-1996_08
Patent number
US05550152

Reaction notes

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