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

HRID 1250334Notes

Reaction equation

HRID 1250334 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 either 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 either
  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-64baf8365f004ee98d30cb4f09898af2
Source dataset
uspto-grants-2002_01
Patent number
US06337420B1

Reaction notes

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