Methanol → 1-Dimethoxymethyl-4-iodo-benzene

HRID 2225036Notes

Reaction equation

HRID 2225036 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.O.C[CH2:12][O:13]CC.[CH3:16]O>Cl[Ti](Cl)(Cl)Cl>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([O:13][CH3:12])[O:7][CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3283Diethyl EtherHCID 966574-Iodobenzaldehyde

Product 1

HCID 114147591-Dimethoxymethyl-4-iodo-benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

A solution of 4-iodobenzaldehyde (10.0 g, 43.1 mmol) in MeOH (150 mL) was treated with TiCl4 (80 μL, 430 μmol) under argon for 15 min. TEA (0.2 mL) was added. After 15 min, water and Et2O were added. The organic layer was collected, dried (Na2SO4), filtered, and concentrated to give a pale yellow oil (11.5 g, 96%): 1H NMR δ 3.30 (s, 6H), 5.34 (s, 1H), 7.19 (d, J=8.4 Hz, 2H), 7.70 (d, J=8.4 Hz, 2H); 13C NMR δ 52.4, 94.3, 102.1, 128.6, 137.1, 137.6.

Workup

  1. customThe organic layer was collected
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b13d38318a24a25ab60bc8e058c9d4e
Source dataset
uspto-grants-2008_05
Patent number
US07378520B2

Reaction notes

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