Ammonium Chloride → HCID 15294442, compound

HRID 1737191Notes

Reaction equation

HRID 1737191 reaction equation
[Mg].Cl[CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[CH3:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH3:18])[C:16]=1[OH:17])[CH:12]=[O:13].[Cl-].[NH4+]>C(OCC)C>[OH:17][C:16]1[C:15]([CH3:18])=[CH:14][C:11]([CH:12]([CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5])[OH:13])=[CH:10][C:9]=1[CH3:8]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 75361Silane, (chloromethyl)trimethyl-HCID 5462224Magnesium2×

Product 1

HCID 15294442HCID 15294442, compound

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 3,5-dimethyl-4-hydroxybenzaldehyde (1.5 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-3,5-dimethyl-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-4a1a591b373f4f5cbd2ffe751961d4af
Source dataset
uspto-grants-1999_10
Patent number
US05962435

Reaction notes

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