Hydrogen Peroxide → (S)-(+)-5-Hydroxy-2-(2-methylbutyloxy)benzonitrile

HRID 442587Notes

Reaction equation

HRID 442587 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C@@H:11]([CH3:14])[CH2:12][CH3:13])#[N:2].[OH:18]O>C1COCC1>[OH:18][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C@@H:11]([CH3:14])[CH2:12][CH3:13])=[C:3]([CH:4]=1)[C:1]#[N:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 53923893(S)-(+)-3-Cyano-4-(2-methylbutyloxy)phenylboronic acid

Product 1

HCID 54230638(S)-(+)-5-Hydroxy-2-(2-methylbutyloxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound 47 (3.00 g, 0.014 mol), hydrogen peroxide (30% w/v, 150 ml) and THF (200 ml) was heated under reflux for 3 h. The water/THF mixture was removed in vacuo and the oily residue was dissolved in diethyl ether and washed with water. The ether was dried (MgSO4) and evaporated in vacuo to give a viscous, fawn oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customThe water/THF mixture was removed in vacuo
  4. dissolutionthe oily residue was dissolved in diethyl ether
  5. washwashed with water
  6. dry with materialThe ether was dried (MgSO4)
  7. customevaporated in vacuo
  8. customto give a viscous, fawn oil

Sources & evidence

ORD record
ord-b70419c29651497088e7b132a6d6efe6
Source dataset
uspto-grants-1999_04
Patent number
US05891358

Reaction notes

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