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

HRID 1164556Notes

Reaction equation

HRID 1164556 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.O>C(O)C>[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 962WaterHCID 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 702EthanolSolvent

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 milliliters 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-9a6020fbb96549ffa8051e4fe1485510
Source dataset
uspto-grants-1983_01
Patent number
US04370434

Reaction notes

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