Trimethyl orthoformate → HCID 18670342, compound

HRID 1716209Notes

Reaction equation

HRID 1716209 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[C:4]([O:10][CH3:11])[CH:3]=1.[CH:12]([O:17][CH3:18])([O:15][CH3:16])OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:12]([O:15][CH3:16])[O:17][CH3:18])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 110530414-Bromo-2-methoxybenzaldehyde

Product 1

HCID 18670342HCID 18670342, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-bromo-2-methoxybenzaldehyde (1 g, 4.67 mmol) was dissolved in MeOH (20 ml) and trimethyl orthoformate (562 μl, 5.139 mmol) and p-toluene sulphonic acid monohydrate (89 mg, 0.467 mmol) were added to the resulting solution. The mixture was stirred overnight at room temperature and then the solvent was removed under vacuo. The residue was taken up with Et2O and washed with 5% Na2CO3 and with water. The organic phase was dried over Na2SO4 and evaporated to give 1.22 g of 4-bromo-1-dimethoxymethyl-2-methoxy-benzene as a colorless oil.

Workup

  1. customthe solvent was removed under vacuo
  2. washwashed with 5% Na2CO3 and with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-9610402eeecb4b018610cff2c5d8ed8b
Source dataset
uspto-grants-2010_09
Patent number
US07803800B2

Reaction notes

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