O-Xylene → Ethyl 4-(4-methylthiophenoxy)benzoate

HRID 1591106Notes

Reaction equation

HRID 1591106 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.OC1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1.[C:22](=O)([O-])[O-].[K+].[K+].C1(C)C(C)=CC=CC=1>[Cu].O>[CH3:22][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 660374-Bromothioanisole

Product 1

HCID 10778595Ethyl 4-(4-methylthiophenoxy)benzoateYield 36.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

The mixture of 4-bromothioanisole (10.0 g, 49.2 mM), ethyl 4-hydroxybenzoate (8.17 g, 49.2 mM), potassium carbonate (6.80 g, 49.2 mM), copper (0.5 g) and xylene (300 ml) was stirred for 24 h under reflux. The mixture was cooled to the room temperature and poured into water. The mixture was filtered through celite, and the toluene solution was washed with water and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give ethyl 4-(4-methylthiophenoxy)benzoate (4.86 g, 36%) as colorless crystals, m.p. 46.4° C.

Workup

  1. temperatureunder reflux
  2. filtrationThe mixture was filtered through celite
  3. washthe toluene solution was washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-a92f9a95325b4e748fedf2f2f685ecfc
Source dataset
uspto-grants-1993_04
Patent number
US05206259

Reaction notes

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