Hydrochloric Acid → Methyl 2-allyloxy-3-formyl-4-methoxybenzoate

HRID 1370163Notes

Reaction equation

HRID 1370163 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH-].[K+].[OH:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].Cl>CS(C)=O>[CH2:1]([O:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 219335993-Formyl-2-hydroxy-4-methoxy-benzoic acid methyl ester

Product 1

HCID 21933587Methyl 2-allyloxy-3-formyl-4-methoxybenzoateYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

At room temperature, 23.2 g (0.192 mol) of allyl bromide were added dropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and 20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 4 hours. The mixture was subsequently added to 1.5 l of 3% strength aqueous hydrochloric acid with stirring and extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. Chromatography over silica gel using cyclohexane/ethyl acetate=1:2 gave 7.7 g (36% of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.

Workup

  1. stirringwith stirring
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. customdried
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-18550df5653244d5a1c3a918df1d680d
Source dataset
uspto-grants-2003_06
Patent number
US06583089B1

Reaction notes

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