Water → HCID 68643629, compound

HRID 1987478Notes

Reaction equation

HRID 1987478 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-4e56929d85384e3593a65b0593a649ac
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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