Thiophenol → HCID 54231216, compound

HRID 1086762Notes

Reaction equation

HRID 1086762 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COCCOC.[Na].[O:15]([C:22]1[CH:23]=[C:24]([CH:34]=[CH:35][CH:36]=1)[O:25][C:26](F)=[C:27]([F:32])[C:28]([F:31])([F:30])[F:29])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[O:15]([C:22]1[CH:23]=[C:24]([CH:34]=[CH:35][CH:36]=1)[O:25][C:26]([S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[C:27]([F:32])[C:28]([F:29])([F:30])[F:31])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 80711,2-DimethoxyethaneHCID 5360545SodiumHCID 53725492HCID 53725492, compound

Product 1

HCID 54231216HCID 54231216, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Eleven g (0.1 mole) of thiophenol and 150 ml 1,2-dimethoxy ethane are placed into a flask and stirred under nitrogen while 2.3 g of metal sodium are added in portions. When this reaction is complete, 32 g of 1-(3-phenoxyphenoxy)perfluoropropene are added dropwise causing a slight exotherm. The mixture is stirred at 75° C. for six hours following this addition. After cooling, 150 ml of dilute base water solution is added and the mixture is stirred. The product layer is separated and washed with 150 ml water, separated, dried over sodium sulfate, filtered and distilled to produce the title compound as an oil in a yield of 38 percent. The oil has a pour point of -26° C. and a boiling range of 150° to 190° C. at 0.5 mm Hg.

Workup

  1. additionare added in portions
  2. additionthis addition
  3. temperatureAfter cooling
  4. stirringthe mixture is stirred
  5. customThe product layer is separated
  6. washwashed with 150 ml water
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. distillationdistilled

Sources & evidence

ORD record
ord-e7c45e72b2ff4d3ab087475bbf7ac0de
Source dataset
uspto-grants-1991_07
Patent number
US05032301

Reaction notes

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