Water → Ethanone, 2-(diphenylphosphinothioyl)-1-phenyl-

HRID 1371244Notes

Reaction equation

HRID 1371244 reaction equation
[C:1]1([PH:7](=[S:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].[OH-].[K+].O>C(Cl)Cl>[C:19]1([C:17]([CH2:16][P:7](=[S:14])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:18])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 107572-ChloroacetophenoneHCID 14797Potassium HydroxideHCID 178528040HCID 178528040, compound

Product 1

HCID 614971Ethanone, 2-(diphenylphosphinothioyl)-1-phenyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of diphenylphosphine sulfide (0.218 g, 0.001 mol) and chloroacetophenone (0.216 g, 0.0014 mol) in methylene chloride (4 ml) was cooled to 8–10° C. in an ice-water bath. Small pieces of solid potassium hydroxide (0.196 g, 0.0035 mol) were added while stirring under nitrogen atmosphere. After 45 minute, water (2 ml) was added and the organic layer was separated, washed with more water (2 ml) and dried over sodium sulfate. The solvent was removed under reduced pressure using a rotary evaporator and the oily residue was crystallized from ethyl acetate-hexane mixture to give 0.19 g (56.5%) of star shaped crystals. mp=83–84° C.

Workup

  1. temperaturewas cooled to 8–10° C. in an ice-water bath
  2. customthe organic layer was separated
  3. washwashed with more water (2 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customa rotary evaporator
  7. customthe oily residue was crystallized from ethyl acetate-hexane mixture
  8. customto give 0.19 g (56.5%) of star

Sources & evidence

ORD record
ord-d9125d3c4a3b428e8432974472c5764b
Source dataset
uspto-grants-2007_01
Patent number
US07157219B2

Reaction notes

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