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

HRID 2379597Notes

Reaction equation

HRID 2379597 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-5a1f13566d7547879dd523016277dc1c
Source dataset
uspto-grants-1994_11
Patent number
US05362878

Reaction notes

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