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Metandienone Wikipedia

1,2,3‑Trimethoxy‑4‑phenylbenzene (also called TMB or Trimethoxyphenylbenzene)

A yellowish solid that is insoluble in water but soluble in most organic solvents such as dichloromethane, ethyl acetate, acetone and ethanol. It is commonly obtained by the alkylation of a phenol derivative with methyl iodide under basic conditions.

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Physical Data

Property Value

Appearance Yellowish solid

Melting point ~138 °C (decomposes)

Boiling point Not available – decomposes on heating

Density 1.15 g cm⁻³ (at 20 °C)

Solubility Insoluble in water; soluble in CH₂Cl₂, EtOAc, MeOH, EtOH

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Synthetic Routes

1. Friedel–Crafts Alkylation of Phenol

Phenol + CH₃I (10 equiv.) + AlCl3 (20 % excess) → 2‑methoxy‑4‑methylphenol

Reaction Conditions: 0 °C to room temperature, 6–12 h.

Purification: Flash chromatography (silica gel, hexane/EtOAc gradient).

2. Methylation of Hydroxyl Group Followed by Friedel–Crafts Alkylation

Phenol + MeI (1.5 equiv.) → anisole
Anisole + CH₃I (10 equiv.) + AlCl3 (20 % excess) → 2‑methoxy‑4‑methylphenol

Advantages: Avoids over‑alkylation of the aromatic ring.

Key Reaction Conditions

Step Reagent Quantity (g, mmol) Solvent Temperature Time

Friedel–Crafts AlCl₃ (10 % excess over CH₃I) 0.75 g (5.25 mmol) None RT (20‑25 °C) 30 min

Add CH₃I 1.0 g (3.44 mmol) - - - -

Stir – – – – –

Quench H₂O (50 mL) – – – –

Extract EtOAc (3×30 mL) – – – –

Notes:

The reaction is run under anhydrous conditions; moisture can quench the reaction.

Use a sealed tube or Schlenk line to avoid exposure of CH₃I to air.

The final yield may be affected by incomplete extraction; ensure thorough extraction and proper drying over Na₂SO₄ before evaporation.

Answer:

The compound is 4‑chloro‑2‑methoxy‑5‑methylphenyl piperidine, with the piperidine nitrogen attached to the 4‑chloro‑2‑methoxy‑5‑methylphenyl ring. The reaction proceeds via a nucleophilic aromatic substitution (SNAr) of the chlorinated anisole by the amine, followed by protonation of the resulting aniline with HCl to give the hydrochloride salt. The detailed synthetic procedure is given above.
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