Methanol → 3-(Dimethoxymethyl)thiophene

HRID 974076Notes

Reaction equation

HRID 974076 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[CH:8]([O-])([O-])[O:9]C.[CH3:13]O>>[CH3:13][O:7][CH:6]([O:9][CH3:8])[C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 681353-ThiophenecarboxaldehydeHCID 53629101Methylorthoformate

Product 1

HCID 159181383-(Dimethoxymethyl)thiophene

Procedure

224 g of 3-thiophenecarbaldehyde and 265 g of methyl orthoformate are dissolved in 200 ml of methanol. One g of strongly acidic ion-exchange resin Amberlite IR-120(H+) [manufactured by Rohm & Haas] is added thereto, and the mixture is refluxed with heating for 2 hours. The resin is separated by filtration, and the filtrate is condensed under reduced pressure. The residue is distilled to give 294 g of 3-dimethoxymethylthiophene.

Workup

  1. additionOne g of strongly acidic ion-exchange resin Amberlite IR-120(H+) [manufactured by Rohm & Haas] is added
  2. temperaturethe mixture is refluxed
  3. temperaturewith heating for 2 hours
  4. customThe resin is separated by filtration
  5. customcondensed under reduced pressure
  6. distillationThe residue is distilled

Sources & evidence

ORD record
ord-5ee2609a3a77493595776e88de6eac7b
Source dataset
uspto-grants-1991_11
Patent number
US05066669

Reaction notes

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