Ethanol → 1,3-Bis(phenylsulfanyl)propan-2-yl prop-2-enoate

HRID 1902382Notes

Reaction equation

HRID 1902382 reaction equation
C1(S)C=CC=CC=1.[CH2:8]([S:20][CH2:21][CH2:22][C:23]([O:25][CH:26]([CH2:41][S:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]CCCCCC)[CH2:27][S:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]CCCCCC)=[O:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]CCCCCC.C([O-])(=O)C=C.C(O)C>O>[C:23]([O:25][CH:26]([CH2:27][S:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:41][S:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)(=[O:24])[CH:22]=[CH2:21].[C:8]1([S:20][CH2:21][CH2:22][C:23]([O:25][CH:26]([CH2:27][S:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:41][S:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[O:24])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 7969Thiophenol2×HCID 25188AcrylateHCID 54113391HCID 54113391, compound

Product 2

HCID 230705341,3-Bis(phenylsulfanyl)propan-2-yl prop-2-enoateHCID 53839207HCID 53839207, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-bis(phenylthio)-2-propyl acrylate was prepared by using benzenethiol in place of dodecanethiol in the procedures described in Steps (1) and (2) of Example 1. A solution of 15 grams of the acrylate, 5 grams of benzenethiol, and 1 milliliter of "Triton B" in 75 millilters of ethanol was heated under reflux for 51/2 hours. The reaction mixture was allowed to cool and was then poured into water. The oil which precipitated was separated by extraction with toluene. The toluene solution was stripped of solvent on a rotary evaporator leaving 19.8 grams of 1,3-bis-(phenylthio)-2-propyl 3-(phenylthio)propionate which was identified by means of its NMR spectrum.

Workup

  1. temperatureunder reflux for 51/2 hours
  2. temperatureto cool
  3. customThe oil which precipitated
  4. customwas separated by extraction with toluene
  5. customThe toluene solution was stripped of solvent on a rotary evaporator

Sources & evidence

ORD record
ord-3d4e6948e56442d3af371f5a7e67cfad
Source dataset
uspto-grants-1982_12
Patent number
US04362887

Reaction notes

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