Ammonium Chloride → 4-Hydroxy-2,3,5-trimethyl-alpha-[(trimethylsilyl)methyl]benzenemethanol

HRID 975483Notes

Reaction equation

HRID 975483 reaction equation
[Mg].Cl[CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[CH3:8][C:9]1[C:16]([CH3:17])=[C:15]([OH:18])[C:14]([CH3:19])=[CH:13][C:10]=1[CH:11]=[O:12].[Cl-].[NH4+]>C(OCC)C>[OH:18][C:15]1[C:14]([CH3:19])=[CH:13][C:10]([CH:11]([CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5])[OH:12])=[C:9]([CH3:8])[C:16]=1[CH3:17]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 75361Silane, (chloromethyl)trimethyl-HCID 5462224Magnesium2×HCID 108990214-Hydroxy-2,3,5-trimethylbenzaldehyde

Product 1

HCID 199719594-Hydroxy-2,3,5-trimethyl-alpha-[(trimethylsilyl)methyl]benzenemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

Mix magnesium turnings (240 mg, 10 mmol) and anhydrous ethyl ether under an inert atmosphere. Add a solution of chloromethyltrimethylsilane (1.9 g, 10 mmol) in anhydrous ethyl ether. Stir until the magnesium metal dissolves. Add a solution of 2,3,5-trimethyl-4-hydroxybenzaldehyde (1.7 g, 10 mmol) in anhydrous ethyl ether. Stir until reaction is complete. Cool the reaction mixture to 0° C. and add saturated ammonium chloride solution. Separate the ether layer, wash with water and dry (MgSO4). Evaporate to give 4-hydroxy-2,3,5-trimethyl-α-[(trimethylsilyl)methyl]benzenemethanol and purify by silica gel chromatrography.

Workup

  1. dissolutiondissolves
  2. customSeparate the ether layer
  3. washwash with water
  4. dry with materialdry (MgSO4)
  5. customEvaporate

Sources & evidence

ORD record
ord-7c3924ca28dc41a9a07aa01e0ef1519f
Source dataset
uspto-grants-1997_03
Patent number
US05608095

Reaction notes

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