Methanol → HCID 1531420, compound

HRID 1957490Notes

Reaction equation

HRID 1957490 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.Cl[CH2:21]Cl.CO>O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5]([O:7][CH3:21])=[O:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 102762,4,5-Trimethoxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 1531420HCID 1531420, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To 21.2 g of 2,4,5-trimethoxybenzoic acid, 30 ml of thionyl chloride were added at room temperature, followed by heating under reflux for 4 hours. The reaction mixture was thereafter distilled off under reduced pressure. To the residue so obtained, 50 ml of dichloromethane, 10 ml of methanol and 20 ml of triethylamine were added, followed by stirring under ice cooling for one hour. After the completion of the reaction, water was added to the reaction mixture, followed by extraction with chloroform. The extract was washed successively with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, water and saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, whereby a crude product was obtained. The crude product so obtained was washed with methanol, whereby 14.6 g of methyl 2,4,5-trimethoxybenzoate were obtained (yield: 65%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. distillationThe reaction mixture was thereafter distilled off under reduced pressure
  4. customTo the residue so obtained
  5. additionwas added to the reaction mixture
  6. extractionfollowed by extraction with chloroform
  7. washThe extract was washed successively with 1N hydrochloric acid
  8. dry with materiala saturated aqueous solution of sodium bicarbonate, water and saturated saline and then dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure, whereby a crude product
  10. customwas obtained
  11. customThe crude product so obtained
  12. washwas washed with methanol

Sources & evidence

ORD record
ord-508ded54f5694a398addd5086c16bd41
Source dataset
uspto-grants-1998_07
Patent number
US05786355

Reaction notes

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