Sodium → HCID 21311730, compound

HRID 971824Notes

Reaction equation

HRID 971824 reaction equation
[Na].[C:2]1([CH:8]([OH:11])[CH2:9][SH:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:12]([CH:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:13]>C1(C=CC(O)=CC=1)O.C(O)C>[C:2]1([CH:8]([OH:11])[CH2:9][S:10][CH:14]([CH:12]=[CH2:13])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5360545Sodium2×HCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 1204861428713-50-0

Product 1

HCID 21311730HCID 21311730, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 702EthanolSolvent

Procedure

To 125 ml of absolute ethanol was added 5.7 g (0.247 moles) of sodium metal. After the sodium had dissolved, the solution was cooled to 0° to 5° C. and 38 g (0.247 moles) of 1-phenyl-2-mercaptoethanol was added dropwise. After addition, the reaction was stirred at 0° to 5° C. for 1 hour and then 37.7 g (0.247 moles) of vinylbenzyl chloride was added dropwise. After the addition was complete, 0.5 g of hydroquinone was added and the mixture was refluxed for 2 hours. The mixture was cooled and the sodium chloride was removed by filtration. The solvent was evaporated and the residue was added to 100 ml of water. The aqueous mixture was extracted with three 100 ml portions of ether and the combined ethereal extracts were dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated to leave 70 g of the product as a crude oil. Due to its high boiling point, the product was used without further purification in the synthesis of the following sulfone.

Workup

  1. temperaturethe solution was cooled to 0° to 5° C.
  2. additionAfter addition
  3. additionAfter the addition
  4. temperaturethe mixture was refluxed for 2 hours
  5. temperatureThe mixture was cooled
  6. customthe sodium chloride was removed by filtration
  7. customThe solvent was evaporated
  8. additionthe residue was added to 100 ml of water
  9. extractionThe aqueous mixture was extracted with three 100 ml portions of ether
  10. dry with materialthe combined ethereal extracts were dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe solvent evaporated

Sources & evidence

ORD record
ord-b1d768ecc4c841f4b872a4d82e60c010
Source dataset
uspto-grants-1979_07
Patent number
US04161407

Reaction notes

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