Methanol → 1-Bromo-4-(dimethoxymethyl)benzene

HRID 129561

Reaction equation

HRID 129561 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([O-])([O-])[O:11]C.[CH3:15]O>C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([O:11][CH3:10])[O:7][CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 707414-BromobenzaldehydeHCID 53629101Methylorthoformate

Product 1

HCID 6883421-Bromo-4-(dimethoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 4-bromobenzaldehyde (21.9 g, 120 mmol), methyl orthoformate (50 mL, 457 mmol), and para-toluenesulfonic acid (0.05 g, 0.29 mmol) in 100 mL of methanol was heated under reflux for 5 hours. The solvent was removed under vacuum and distillation of the remaining residue gave 1-bromo-4-(dimethoxymethyl)benzene (2.24 g, 9.7 mmol) as a clear colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvent was removed under vacuum and distillation of the remaining residue

Sources & evidence

ORD record
ord-982932756d994372a643c2242b12ec62
Source dataset
uspto-grants-1995_11
Patent number
US05468867

Linked notes

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