Dimethyl Sulfide → 4-(2-Hydroxybenzyl)phenylacetonitrile

HRID 1982821Notes

Reaction equation

HRID 1982821 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-bd9f206cd4a046c799edbdbbd334a03f
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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