Ethanol → HCID 4496358, compound

HRID 1075398Notes

Reaction equation

HRID 1075398 reaction equation
[O:1]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[O:1]([CH:8]([CH3:12])[C:9]([O:11][CH2:18][CH3:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13658DL-2-Phenoxypropionic acid

Product 1

HCID 4496358HCID 4496358, compoundYield 94.3%

Procedure

Phenoxypropionic acid (6.64 g, 0.04 mol) is mixed with excess ethanol (10 ml) and concentrated sulfuric acid (0.5 ml) is added. The reaction mixture is refluxed for 3 hours, cooled to room temperature and concentrated. The residue is washed with 1N NaOH and brine, dried (Na2SO4), and concentrated to yield 7.32 g (94.3% yield) of the ester which can be used directly for the subsequent reaction without further purification. 1H nmr (CDCl3) δ: 7.22-7.29 (overlap 2H, phenyl H), 6.88-6.966 (overlap 3H, phenyl H), 4.10-4.20 (overlap 4H, 2CH2O), 2.73 (t, 2H. J=6.4 Hz, CH2), 1.23 (t, 3H, J=7.1 Hz, CH3); 13C nmr (CDCl3) δ: 170.7, 158.7, 129.4(2C), 120.9 114.6(2C), 63.4, 60.5, 34.5, 14.1.

Workup

  1. additionis added
  2. temperatureThe reaction mixture is refluxed for 3 hours
  3. concentrationconcentrated
  4. washThe residue is washed with 1N NaOH and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c7efb4eeafe24d42b48c16d6c34e8795
Source dataset
uspto-grants-1999_05
Patent number
US05900485

Reaction notes

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