Diethyl Ether → 4-(1-Hydroxy-1,3,3-trimethyl-butyl)-benzonitrile

HRID 911666Notes

Reaction equation

HRID 911666 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:12]([Mg]Cl)[C:13]([CH3:16])([CH3:15])[CH3:14].C(OCC)C>C(OCC)C.C1COCC1>[OH:3][C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)([CH3:2])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 740444'-CyanoacetophenoneHCID 178418809HCID 178418809, compound

Product 1

HCID 576565864-(1-Hydroxy-1,3,3-trimethyl-butyl)-benzonitrileYield 24%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-acetylbenzonitrile (1 g, 6.88 mmol) in diethyl ether/THF (1:1, 60 mL) and cool the solution to 0° C. Add 1M neopentylmagnesium chloride in diethyl ether (8.3 mL, 8.3 mmol) under nitrogen and stir the mixture at room temperature overnight. Add saturated aqueous NH4Cl and extract the mixture twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1, 9:1) to give the desired intermediate (364 mg, 24%).

Workup

  1. extractionAdd saturated aqueous NH4Cl and extract the mixture twice with EtOAc
  2. dry with materialDry the combined organic extracts over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1, 9:1)

Sources & evidence

ORD record
ord-e768a8c581cb41d1bfd8dc1e837ab8f4
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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