Trimethyl orthoformate → HCID 18670342, compound

HRID 556283Notes

Reaction equation

HRID 556283 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-2429258e67254a0fbe5d72de9005ff1f
Source dataset
uspto-grants-2011_11
Patent number
US08058273B2

Reaction notes

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