Tetrahydrofuran → 2,3,4-Trimethoxybenzaldehyde

HRID 1457614Notes

Reaction equation

HRID 1457614 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[O:11][CH3:12].[O:13]1CCC[CH2:14]1.CCCCCC.C([Li])(CC)C>C(O)(=O)C.CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([O:11][CH3:12])=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][C:8]=1[CH:14]=[O:13]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 124621,2,3-TrimethoxybenzeneHCID 178418400CID 53628100

Product 1

HCID 750062,3,4-TrimethoxybenzaldehydeYield 24%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixed solution of 20 g of 1,2,3-trimethoxybenzene and 100 ml of tetrahydrofuran (THF) was cooled to -78° C., and 140 ml of a hexane solution containing 1M sec-butyl lithium (sec-BuLi) was added dropwise thereto. After stirring the mixture at the same temperature for 45 minutes, 11 ml of dimethylformamide (DMF) was added to the reaction mixture. The mixture was stirred at -50° C. or lower for 45 minutes. Then, a 10% acetic acid aqueous solution was added to the mixture, and the resulting mixture was extracted with diethyl ether. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=9:1) to give 5.7 g of 2,3,4-trimethoxybenzaldehyde (yield: 24%, oily product).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at -50° C. or lower for 45 minutes
  3. extractionthe resulting mixture was extracted with diethyl ether
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-178ab3e6c4fd4e91ad6328782956c104
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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