Water → HCID 68643629, compound

HRID 1158200Notes

Reaction equation

HRID 1158200 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][CH3:18])=[O:10].[Al+3].[Cl-].[Cl-].[Cl-].C(S)CCCCCCCCCCC.O>CCCCCC.C(OCC)(=O)C>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][CH3:18])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 81951-DodecanethiolHCID 6451240Aluminum(III) ChlorideHCID 247227562-Methoxy-2'-thiomethylbenzophenone

Product 1

HCID 68643629HCID 68643629, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of 1.45 g (2-methoxyphenyl)(2-(methylthio)phenyl)methanone (G) and 1.437 g AlCl3 was added slowly 5 mL 1-dodecanethiol. The reaction was stirred overnight before 30 ml water was added. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried over magnesium sulfate, and the volatiles removed by distillation under nitrogen. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.807 g product (3.31 mmol, 60% yield).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe volatiles removed by distillation under nitrogen

Sources & evidence

ORD record
ord-6e1ef128ff5944eb8f20b504429156d4
Source dataset
uspto-grants-2010_10
Patent number
US07807713B2

Reaction notes

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