Water → HCID 19373446, compound

HRID 256631Notes

Reaction equation

HRID 256631 reaction equation
[C:1]([C:6]1[CH:23]=[C:22]([C:24]([CH2:27][CH3:28])([CH3:26])[CH3:25])[CH:21]=[CH:20][C:7]=1[O:8][C:9]1[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2].O.CCCCCCC.C(OCC)(=O)C>Br.CC(O)=O>[C:1]([C:6]1[CH:23]=[C:22]([C:24]([CH2:27][CH3:28])([CH3:26])[CH3:25])[CH:21]=[CH:20][C:7]=1[O:8][C:9]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8900HeptaneHCID 19373470HCID 19373470, compound

Product 1

HCID 19373446HCID 19373446, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A solution of 2-(2,4-di-tert-pentylphenoxy)-5-methoxybenzoic acid (10.0 g, 0.026 mol) in 31% HBr/HOAc (100 mL) was heated to reflux for 1 hour. The reaction mixture was cooled to room temperature and added to 500 mL water. The mixture was extracted with ethyl acetate (3×200 mL), and the combined organic extracts repeatedly washed with water to remove traces of acid. The organic extracts were dried over magnesium sulfate and concentrated to give a tan solid. Chromatography on silica gel with 1:1 heptane:ethyl acetate yielded the product in 80% yield. NMR and mass spectral data were consistent with the proposed structure.

Workup

  1. temperatureto reflux for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  3. washthe combined organic extracts repeatedly washed with water
  4. customto remove traces of acid
  5. dry with materialThe organic extracts were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a tan solid

Sources & evidence

ORD record
ord-de5e61d833e442d097afb9158d87b9e2
Source dataset
uspto-grants-1993_11
Patent number
US05258407

Reaction notes

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