Ethanol → HCID 15718055, compound

HRID 982446Notes

Reaction equation

HRID 982446 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[CH2:18](O)[CH3:19]>S(=O)(=O)(O)O>[CH2:18]([O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=1[O:5][C:4]1[CH:15]=[CH:16][CH:17]=[C:2]([OH:1])[CH:3]=1)[CH3:19]

Participants

4

Reactant 2

HCID 702EthanolHCID 15718054HCID 15718054, compound

Product 1

HCID 15718055HCID 15718055, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 17.8 g of 2-(3-hydroxyphenoxy)benzoic acid in 250 ml of ethanol and 1 ml of sulfuric acid was heated at reflux for two days. After cooling, the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was dried and concentrated in vacuo. The resulting residue was purified by high pressure liquid chromatography eluting with a 0-30% ethyl acetate in hexane gradient. The appropriate fractions were combined and concentrated in vacuo to provide 16.78 g of the desired subtitled intermediate as an oil.

Workup

  1. temperatureat reflux for two days
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by high pressure liquid chromatography
  8. washeluting with a 0-30% ethyl acetate in hexane gradient
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-196993b3b2b1438780292e46c3f11d52
Source dataset
uspto-grants-1991_02
Patent number
US04996230

Reaction notes

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