Potassium Carbonate → Ethyl 2-(4-t-Butylphenylthio)octanoate

HRID 2257157Notes

Reaction equation

HRID 2257157 reaction equation
Br[CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:14]([C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:14]([C:18]1[CH:19]=[CH:20][C:21]([S:24][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:22][CH:23]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754544-Tert-ButylbenzenethiolHCID 95580Ethyl 2-bromooctanoate

Product 1

HCID 14995385Ethyl 2-(4-t-Butylphenylthio)octanoateYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.0 g (0.02 mole) ethyl 2-bromooctanoate, 3.37 g (0.02 mole) p-t-butylthiophenol and 3.31 g (0.24 mole) potassium carbonate in 70 ml acetone was refluxed under nitrogen overnight. The reaction mixture was cooled to room temperature and filtered and the filtrate was concentrated in vacuo. The residue was chromatographed on 500 g silica gel, eluting with 6:4 methylene chloride/hexane to yield 3.8 g (57% yield) of the desired product as an oil.

Workup

  1. temperaturewas refluxed under nitrogen overnight
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on 500 g silica gel
  5. washeluting with 6:4 methylene chloride/hexane

Sources & evidence

ORD record
ord-2b03c1ed92614a51bfc64c6129588c3d
Source dataset
uspto-grants-1997_08
Patent number
US05656634

Reaction notes

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