Water → 1-(Ethylsulfanyl)hept-1-ene

HRID 2083686Notes

Reaction equation

HRID 2083686 reaction equation
[CH2:1]([S:3][CH:4](SCC)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2].O.C(S)C>P(=O)(O)(O)O.CCOCC>[CH2:1]([S:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6343EthanethiolHCID 10867824HCID 10867824, compound

Product 1

HCID 540122511-(Ethylsulfanyl)hept-1-eneYield 78%

Reagents, catalysts & solvents 2

HCID 1004Phosphoric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1,1-di(ethylthio)-heptane (54.5 g., 10.25 mole) and 10 drops of 89% phosphoric acid is heated in a Claisen flask at a pressure of 200-250 mm. Care is taken that the vapor temperature does not exceed 165°. The receiver is cooled with water so that ethanethiol does not condense. The distillate is diluted with ether and washed with 2 N sodium hydroxide and water and dried. Distillation (87°-90°/12 mm.) afforded 1-ethylthio-1-heptene (30 g., 78%), nD20 1.4760.

Workup

  1. temperatureis heated in a Claisen flask at a pressure of 200-250 mm
  2. customdoes not exceed 165°
  3. customcondense
  4. washwashed with 2 N sodium hydroxide and water
  5. customdried
  6. distillationDistillation (87°-90°/12 mm.)

Sources & evidence

ORD record
ord-a14799b045364658ac8eecb97a9f01ac
Source dataset
uspto-grants-1978_04
Patent number
US04086278

Reaction notes

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