Water → 2-(2-(Methylthio)benzyl)phenol

HRID 1158201Notes

Reaction equation

HRID 1158201 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][CH3:17])=O.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.O>CCCCCC.C(OCC)(=O)C>[CH3:17][S:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68643629HCID 68643629, compound

Product 1

HCID 686436452-(2-(Methylthio)benzyl)phenolYield 74%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of 0.337 g (2-hydroxyphenyl)(2-(methylthio)phenyl)methanone (H) (1.38 mmol) and 0.5 ml triethylsilane was added 2 ml TFA. After 1 h, water was added and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, and concentrated. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.235 g product (1.02 mmol, 74% yield).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b1fb818e78ab409e8dce39904bbb90a2
Source dataset
uspto-grants-2010_10
Patent number
US07807713B2

Reaction notes

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