Ethanol → HCID 86648894, compound

HRID 1094479Notes

Reaction equation

HRID 1094479 reaction equation
Br[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[O:10](CC)[C:11]([S-:13])=[S:12].[K+].[CH2:17](O)[CH3:18]>>[O:10]([CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3])[C:11]([S:13][CH2:17][CH3:18])=[S:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 11454(1-Bromoethyl)benzeneHCID 2735045Potassium ethylxanthate

Product 1

HCID 86648894HCID 86648894, compound

Procedure

A 500 mL round bottom 3 neck flask was fitted with a magnetic stirrer, nitrogen inlet, and a temperature probe, 1-bromoethyl benzene (20.5 mL) and 200 mL absolute ethanol were added. The reaction flask was placed in an ice/water bath at 0° C. Potassium O-ethyl xanthate was added slowly using a powder funnel rinsed into the reaction flask with an additional 100 mL ethanol. The reaction flask was allowed to stir for an additional 24 hours at room temperature and then 250 mL of purified water was added. The crude mixture was extracted 4 times with 200 mL of 2:1 heptane:ethyl ether retaining the organic layers. The combined organic layers were dried over anhydrous sodium sulfate, filtered and the solvent was removed under reduced pressure to yield 31.42 grams of crude product. A portion, 15 grams, of the crude product was eluted from a silica gel column using hexane to give 12.81 grams of the pure product.

Workup

  1. customA 500 mL round bottom 3 neck flask was fitted with a magnetic stirrer, nitrogen inlet
  2. customThe reaction flask was placed in an ice/water bath at 0° C
  3. washrinsed into the reaction flask with an additional 100 mL ethanol
  4. addition250 mL of purified water was added
  5. extractionThe crude mixture was extracted 4 times with 200 mL of 2:1 heptane
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customto yield 31.42 grams of crude product
  10. washA portion, 15 grams, of the crude product was eluted from a silica gel column

Sources & evidence

ORD record
ord-256090f5432443188199a1828aa9319c
Source dataset
uspto-grants-2012_03
Patent number
US08133960B2

Reaction notes

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