Methanol → Methyl [p-(phenoxy)phenyl]acetate

HRID 491056Notes

Reaction equation

HRID 491056 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:23]O>>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]([O:17][CH3:23])=[O:16])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2390774-Phenoxyphenylacetic acid

Product 1

HCID 12531834Methyl [p-(phenoxy)phenyl]acetate

Procedure

To a solution of 4-phenoxyphenylacetic acid (1.0 g, 4.38 mmoles) in methanol (5.0 ml) was added concentrated sulfuric acid (0.05 ml, 0.88 mmoles) and the mixture was heated to reflux for about 5 hours. The mixture was cooled and concentrated under reduced pressure. To the residue was added a saturated aqueous solution of sodium bicarbonate (20.0 ml) and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and evaporated to dryness to afford the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 5 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate (20.0 ml)
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe combined organic extracts were washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-c657ae2421a44cdeb96773c56eefeec5
Source dataset
uspto-grants-2009_05
Patent number
US07528282B2

Reaction notes

Loading…