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

HRID 2041528Notes

Reaction equation

HRID 2041528 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 1 M 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-4eca9dbb1d7645d4a8ff5b4af27fde3f
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

Loading…