Methanethiol → HCID 21556999, compound

HRID 267365Notes

Reaction equation

HRID 267365 reaction equation
[CH3:1][SH:2].[CH2:3]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)[C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1.[OH-].[K+]>C(COC)OC>[CH2:3]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][S:2][CH3:1])[C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 14797Potassium HydroxideHCID 21557029HCID 21557029, compound

Product 1

HCID 21556999HCID 21556999, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl mercaptan, 1.6 g. (0.032 mole) was bubbled into a solution of 13.0 g. (0.032 mole) of 12-bromododecyl piperonyl ether, and 5.6 g. (0.1 mole) of potassium hydroxide in 150 ml. of dimethoxyethane. When all had been added the resulting mixture was heated at reflux for 3 hours. After cooling and filtering, the solvent was removed by evaporation. The crude product was then dissoved in hexane and filtered. The filtrate was evaporated to give 8.5 g. of oily product. The NMR spectra was consistent with the assigned structure. The infrared spectra had strong adsorption peaks at 3.4, 3.5, 6.7, 6.95, 8.0, 9.0, 9.6, 10.6 and 12.2 microns. Analysis was as follows:

Workup

  1. custom(0.032 mole) was bubbled into a solution of 13.0 g
  2. additionWhen all had been added the resulting mixture
  3. temperaturewas heated
  4. temperatureat reflux for 3 hours
  5. temperatureAfter cooling
  6. filtrationfiltering
  7. customthe solvent was removed by evaporation
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. customto give 8.5 g

Sources & evidence

ORD record
ord-4420c56c491a4e06adff9ce308770d80
Source dataset
uspto-grants-1976_03
Patent number
US03941884

Reaction notes

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