Dimethyl Sulfide → 4-(2-Hydroxybenzyl)phenylacetonitrile

HRID 1826631Notes

Reaction equation

HRID 1826631 reaction equation
FC(F)(F)C(O)=O.CSC.C([O:18][C:19]1[CH:34]=[CH:33][CH:32]=[CH:31][C:20]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=1)C1C=CC=CC=1>O>[OH:18][C:19]1[CH:34]=[CH:33][CH:32]=[CH:31][C:20]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 6422Trifluoroacetic acidHCID 21909295[4-(2-Benzyloxybenzyl)phenyl]acetonitrile

Product 1

HCID 219092754-(2-Hydroxybenzyl)phenylacetonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoroacetic acid (17 mL), water (1 mL) and dimethyl sulfide (2 mL) were added to [4-(2-benzyloxybenzyl)phenyl]-acetonitrile (0.41 g), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1) to give [4-(2-hydroxybenzyl)phenyl]acetonitrile (0.26 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-72b55674f2a24e33ba0b885fe3037614
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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