Thiophenol → HCID 22842163, compound

HRID 1090186Notes

Reaction equation

HRID 1090186 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][CH:7]([CH3:15])[O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)(=O)=O.[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>CCO>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]1[O:8][CH:7]([CH3:15])[CH2:6][CH2:5][S:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 88490870HCID 88490870, compound

Product 1

HCID 22842163HCID 22842163, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of (2) (27.5 g) in EtOH (46 ml) was added dropwise during 10 min to a solution of PhSNa prepared from PhSH (11.2 ml) and Na (3.01 g) in EtOH (130 ml) with stirring at room temperature. The mixture was stirred and heated under reflux for 2.5 hr. The mixture was poured into iced 2N aqueous NaOH and extracted with ether. The ether solution was washed with brine, dried over MgSO4 and concentrated in vacuo to give 22.3 g of (3).

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated
  3. temperatureunder reflux for 2.5 hr
  4. extractionextracted with ether
  5. washThe ether solution was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5212aa2472e84fe0a521268394c467ef
Source dataset
uspto-grants-1992_01
Patent number
US05081152

Reaction notes

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