Hydrochloric Acid → 3,4,5-Trichloro-α-methylbenzenemethanol

HRID 1441034Notes

Reaction equation

HRID 1441034 reaction equation
[Mg].[CH3:2]I.[Cl:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([Cl:14])[C:12]=1[Cl:13])[CH:8]=[O:9].[Cl-].[NH4+].Cl>CCOCC>[Cl:4][C:5]1[CH:6]=[C:7]([CH:8]([OH:9])[CH3:2])[CH:10]=[C:11]([Cl:14])[C:12]=1[Cl:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 141183213,4,5-Trichlorobenzaldehyde

Product 1

HCID 224210533,4,5-Trichloro-α-methylbenzenemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of magnesium turnings (0.55 g.) in dry ether (20 ml.) was added dropwise a solution of methyl iodide (3 g.) in dry ether (10 ml.) at such a rate that the reaction refluxed. After the addition was complete, 3,4,5-trichlorobenzaldehyde (see Process B) (4 g.) was added in dry ether (10 ml.) at a rate that maintained reflux. The reaction was stirred overnight. Saturated ammonium chloride solution was added, followed by dilute hydrochloric acid. The organic layer was separated, dried over anhydrous magnesium sulphate and evaporated to give 1-(3,4,5-trichlorophenyl)ethanol. Nuclear Magnetic Resonance Spectrum (NMR) was as follows; 1.2, 3H, d; 4.2, 1H, s; 4.8, 1H, m; 7.3, 2H, s.

Workup

  1. temperaturerefluxed
  2. additionAfter the addition
  3. temperaturemaintained
  4. temperaturereflux
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-02d0a4fc1c2849e0a111d85884862269
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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